


That kiss

by Echo_Winchester



Category: Supernatural
Genre: Bottom Dean, Dean's First Time, F/M, Female!Castiel - Freeform, Fluff and Smut, Hunting, M/M, Male!Reader insert, Multi, bi fanfiction, gay fanfiction
Language: English
Status: In-Progress
Published: 2017-09-09
Updated: 2018-03-23
Packaged: 2018-12-25 17:08:13
Rating: Explicit
Warnings: Major Character Death
Chapters: 28
Words: 33,484
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12040413
Author URL: https://archiveofourown.org/users/Echo_Winchester/pseuds/Echo_Winchester
Summary: You meet the ever handsome (and drunk) dean Winchester at a bar by the coast. Dean wants to use you to help him open up about himself but you both soon discover there is so much more to a kiss than you'd ever expect.Events take place a significant time after the s12 finale, though Jack is mentioned, he doesn't make an appearence.-update-I figured out how to insert photo's into my story! So, I'll be going back to add photo's that help enhance the visual a bit. If you've found a photo or gif that you think could fit somewhere (that I couldn't find) submit them here: https://www.tumblr.com/blog/lzzywinchester  (it's a lower case "L" not an uppercase "i")





	1. Chapter 1

You've had a long shift. Your boss decided to work you overtime, and the hits just kept coming. It's not that your job was dangerous, just that there were risks involved and you'd frequently end up with cuts and bruises on your way out.

  
You were sore and tired, but the drive home seemed much longer than you were willing to stay in a car for. As a last resort, you decided to head down to Carrie's Cafe; A cute little bar and diner off the side of a pleasant shoreline. You checked the mirror, fixing your hair, and wiping the dust out of your stubble. Then you reached into the back seat, looking for your spare clothes to get out of those stupid work rags they make you wear. Finally feeling presentable, you make your way inside.

  
It's not that busy tonight. There's a few cute girls getting tipsy by the bar, a few strong and handsome looking men playing pool, beer congregating on the little table, like a peanut gallery. But what caught your eye were these two stunning men in plaid sitting by the bar in a booth.

You took a seat at the bar, across from the girls, keeping the booth in sight.  
"Hey sugah," The bartender said. You knew her from school years ago, knowing she was far too smart to be dressing and acting like this (not to mention wasn't southern). "Whatchya getin'?"

"Brandy," You said, tone questioning.

"How'd ya take it?" She winks, and moves to show off her chest a little.

"Brandy... From high school right?" She dropped the act for all of 5 seconds before going back to pretending to wash the counter.

"S'not my name here. It's Tammy." She said, not looking at you.

"Good to know for future reference." A deep voice came out of nowhere. You jumped, not realizing one of the plaid guys had come up behind you. Wow he was gorgeous. His intense green eyes were starting right past you, making flirty eyes at Bra-er... Tammy.

Mr. Handsome Stranger winked at you, obviously drunk, and asked her for another round of whiskey for him and his brother. She obliged, putting her hand over his and winked.

"Anything for you, sugah," she giggled then darted off to make the drinks.

"Names Dean by the way," he said to her, smiling. You blushed at his smile, even though it was obvious it wasn't for you. But he surprises you by turning and shaking your hand.

"Uh... (Y/n)." You say, meeting his gaze, seeing how drunk he actually is now. His cheeks are freckled over the soft pink tone to his skin, he's slouching a bit, and rocking softly as if trying to keep his balance even while sitting. You couldn't help but chuckle. "You alright there, Dean?"

"What, me? Pffffffft I'm fine," he slurred, downing his whiskey like it was just a large shot. Your eyes widened, impressed by his talent.

You offered to help him back over to his seat, but he refused. He insisted he's not that drunk yet, and downed the drink meant for his brother.

You don't know why, but you have this strong urge to want to take care of him. You can see the look in his eyes, even though he's smiling- he's lived through some horrible shit and is trying to drink away the memory. You pay for his drinks instead, then insist he sit and drink some water after.

"Pussy," he calls you, teasingly. You chuckle.

"No, don't have one, but I could probably get some by tonight if I try hard enough," you retort, making Dean almost spit his drink out in laughter. Your comment also earns you a "get it on" look from one of the girls across the bar. You wink in her direction and she giggles.

"So," Dean starts up again, facing you.

"You're here alone. Why?" You look at him, confused. "Well I mean, you-yer- you're a decent looking... Er... Gentleman." You chuckle, but continue listening to this obvious train-wreck of a thought. "You don't have a girl waiting for you?" You laugh at that and look down for a brief moment.

"No, haha" you respond. "Looking for something a little less... Female... Tonight..." You slow your words hoping you didn't just scare him off. You weren't out to drag him to bed or anything (though you wouldn't be opposed to the idea). Your eyes instinctively flick over to his broad shoulders, and up his smooth neck, laced in stubble.

Dean is silent for a minute, then grabs your drink by accident, thinking it was his. He downs it like a thirsty desert hiker would with water. He's silent for a bit longer, before he takes a deep breath, turns and asks you, "Whats it like anyway?... K-kissing another dude?" He clears his throat, trying to hide his face heating up.

You shrug, not being sure how to respond to his inquiry. "Like a kiss," You say. "Except sometimes there's stubble that can poke you in the face." You watch him ponder, able to tell that he's trying to will his drunk brain to ask more. To learn. "Lips are lips, Sweetheart. A kiss is just a kiss."

Dean's now watching you talk, eyeballing your mouth. So you muster some sober courage of your own and lean in.  
Dean freezes solid as your mouth makes contact with his. It was short; no tongue, no holding him desperately like you'd like to. Pure demonstration. Besides, he was far too drunk to do anything further. You weren't that kind of guy.

You pull away slowly, allowing him to let the information of what just happened sink in. You decide that while he's sorting out his confusion, you'd order him some water. Tammy slides it over to you, and gives you a wink before going back to gossiping with the drunk girls. You see Dean's brother flipping through a menu, laptop opened just out of eyesight. "You should sober up," you say. Dean says nothing. "Here," you take his hand, and write your phone number on his forearm. "Text me when the hangover subsides."

You get up to leave, watching Dean's fingers fly up to his lips, touching them like he could still feel yours there. You smile.


	2. Chapter 2

Dean wakes up the next morning, head throbbing. Sam, being the awesome little brother that he is, closed the curtains in the motel, and left the lights off. Even unplugged the clock so he could move around without the light making him want to puke.

Dean stumbles over to the bathroom, groaning and rubbing his eye. He turns on the sink and runs his hands under the warm water, bringing it to his face. After drying off, he notices your handwriting on his arm.

_(Y/N),_  
555-7389  
Call me sometime ;)

Dean squints trying to remember, when suddenly it hits him.

He kissed you.. no, _you_ kissed _him_. His face goes red and eyes go wide.

"I kissed a dude..." He mumbled out loud. "Holy shit..." Dean didn't understand why his heart was racing the way it was... It wasn't a butterfly feeling... More like adrenaline. Like he should be running. Running and never talking about this to anyone.

But the other part of him wanted to get a grip. Explore himself for once. He never got to. He never felt like he could admit what he likes. What he's always wanted to try.  
Dean saves your number into his phone under "Potential" and writes your name in the notes. He's not feeling brave enough to text you today, he decides, but he WILL once this case is over with.

He does, however, decide to text Cass. He was supposed to meet up with him and Sam to help them figure out just what they're dealing with.

Sam walks through the door slowly. He notices the lights are off, so he attempts to be quiet.

"Dean," he whispers. "It's just me." Sam sets the food he brought back with him down on the table, as Dean emerges from the bathroom.

"You're awake?" He questions.

"Yeah. Any word about the case?"

"Talked to a witness this morning. She said her wife had gone out for a drink after a rough day at work, and when she came home, she grabbed all of their belongings, screamed at her, then jumped out of a second story window, yet walked away. Still hasn't come home." Dean scrunched his eyes, thinking this information over.  
"But get this," Sam continued. "She said her 'eyes shined from the light in her flashlight'... And-" he cut dean off before he could speak, "She left all of the silver behind."

"So... Home invading shifter?" Dean leaned against the table, now rummaging through the bag of food Sam brought home. His head still hurt, but he hadn't eaten since before going out and he was starving.

"That's my first guess. I loaded the car with our silver knives just in case." 

"Atta boy." Dean shoved french fries into his mouth, savoring the salty taste. He dug further into the bag and found a bottle of asprin. He chuckled, popping the bottle open and swallowing two.

"Alright, well hit up the scene later today, see if we can find anything we missed." He says.  
"Well, actually, I got a call from the sheriff's office. There's been another case just across town. I think we should go check it out."

"Can we eat first? I'm starving." Dean replies, popping more french fries into his mouth.

"Sure."

**Notes for the Chapter:**

> I didn't like the way I ended this chapter, so I attempted to update it... Well, let's just say that didn't work, so I re-uploaded lmao. I feel much better about this ending and have started writing the third chapter. Enjoy!


	3. Chapter 3

**Summary for the Chapter:**

> **NSFW scene below**

It's been a couple days since your encounter with Mr. Handsome Drunk Stranger. You've decided not to hold it over him that he hasn't called. After all, not many guys are as in-tune with their sexuality as you are. You decide to try your luck at the same bar instead, hoping maybe someone there would be willing to take you for a test drive.

You rummage through your clothes, deciding on a matte black, skin tight t-shirt, some loose fitting jeans, and one of your nice pairs of shoes. After fixing your hair in the mirror and splashing some cologne on your wrists and neck, you head out.

The drive doesn't take long, and once you get there you find that the place is more crowded than last time. Tammy is working again tonight, chatting up some hot guy who looks like he's got money to spend.

"It's too bad you've got that ball an chain on ya fingah," she coos, tracing the bones on his hands. He looked hypnotized. "We coulda had loads of fun." she winked and you could see the blood rush to his face.

"(Y/n)!" She calls, noticing you sitting there. A huge smile breaks across her face and she danced over to you. You nod back, smiling."

"Hey Tammy. Think I could get a rum and coke?" You take a seat between Rich Hottie and this tipsy brunette with her boobs barley being held back by her shirt. You winked at her and she blushed and bit her lip at you. You chat up the brunette (her name is either Viv or Syl; you can't really hear her over the music), and discover she's got a place right down the road. After downing a few shots of your own, you take her up on the offer, and follow her to the door.

On your way out, you swear you saw someone who looked exactly like Mr. Handsome Drunk Stranger, but you were now being pulled out of the bar by your wrists, with no time to see if you were right.

\----

She led you up the stairs, her plump and soft lips on yours, almost the whole way to her apartment. You grabbed her hips as she fumbled for he keys, feeling under her shirt, desperate for skin to skin contact. As she finally found the key and put it in the lock, you saw an opportunity to nip at her neck, causing her to gasp and lean into your touch.

Finally with the door open, the real fun began. She crashed her lips to yours, harder than she had all night. Your tongue poking through to explore this new territory. You latched your hands onto her soft hips, pushing her shirt up with them. She broke the kiss to pull it over her head before she reclaimed her place. You saw an opportunity to surprise her, and leaned your hands down to her knees, pulling her up onto your own hips. Your cock getting harder with the intensity rising. She must've noticed because she's now grinding her hips against you, giving you some much needed friction. She moaned loudly as you trailed your kisses back down to her neck, biting and sucking on the tender skin, leaving small marks. Viv/Syl then began to hike your shirt up, somehow, her grip on our hips stronger. She's either a professional pole dancer, or she's done this before. You were impressed and couldn't help the moan that escaped your own lips. You pushed her up against the wall, possessively, testing the waters to see if she liked to be in control or to surrender it. When she didn't fight back, you kept going, sliding your hand down the back of her panties to squeeze her ass. She moaned into your lips, bucking her hips onto you.

This is where you like to get creative; skillfully, you pushed her up so her legs were now on your shoulders, but her back never left the wall. Your hands were on her stomach, preventing her from moving as you palmed that sweet spot over her leggings. She gasped loudly, surprised and more turned on than she has been all night. You feel smug and look up at her.

"How much do you like these pants?" You ask, voice rough with raw desire.

"I hate them," she growls in return, her blue eyes dilated at the thought of what you're about to do. That's all the green light you need, as you rip into the fabric, tearing a hole right next to the seam. Viv/Syl moans loudly, as her hand grips your hair. That always makes them go wild, you smirk. You push her lacy panties aside, savoring the moment; her taking deep heated breaths, her grip on our hair, the weight of her legs on your shoulders. Then you begin.

You've done this so many times. You were a giver, after all. Oral was your strong suit; for men and women. The moans, cries and borderline screams you were getting out of her let you know you were rocking her world and that only edges on your raging boner. You're holding her up by her ass, hooking your arms underneath her legs to keep them apart. You flatten your tongue, laping up her juices, keeping your teeth against her clit, keeping a slow yet rough momentum. After a few minutes of doing this, you push your tongue inside, humming slightly so she can feel the vibrations.

"Oh god... oh god (y/n)... please..." She cries. You keep going, quickening your pace and alternating between running your tongue up her center and pushing it into her. She's going wild, gripping your hair tighter, legs shaking violently. Her moans and cries get louder and louder and finally she releases. You keep going, milking her through her orgasm as much as you can. Your dick twitches at the cries she makes.

The second her breath slows, you let go of her long enough to unhook your arms, then grip her by the hips before she hits the ground. Locking your lips back with her, she shoves her tongue in your mouth again, holding you desperately. You buck your hips up, rubbing your rock hard cock against her, aching to feel yourself inside her. You carry her over to the bed, and flip her under yourself. As you do that, she growls (actually _growls_ ), and gives you a playful smirk.

You can't help but play along- growling back as you lean in to sink your teeth into her skin. She gasps, pressing her body against yours, as you head south. You nip and suck at her skin until you hit her bra, which you push down, exposing her nipples. Without hesitation you latch on, hearing her groan and hiss. You then pull her up in the same motion as you pull out your throbbing member. As much as you love to tease, if you didn't get some kind of friction other than fabric, you were gonna explode. Thankfully, she knew exactly where you were headed. Viv/Syl pushed you over on your back. Her hair now tangled and poofy only made her look sexier as she gave you a devilish wink. You swallowed hard as you watched her move her head down, moaning loudly when her tongue came into contact with your cock. She trailed her tongue slowly along the side, then back down again, tracing every vein. And though you were enjoying it, you needed more and you were NOT about to beg.

You placed one hand on the back of her head, bucking your hips up to meet her mouth. And just like that, you were in total bliss. Apparently you're not the only oral-professional. She took you down to the base with such ease, it was mind blowing. You couldn't help the loud groan that resonated in your throat.

"F-fuck... oh..." You panted, as she began to bob her head. You could feel the back of her throat as she sucked you in, gripping the base with her hand. Now your own legs were shaking as you felt the heat pool in your gut. You grabbed onto her head, holding it still, as you pumped your hips.

"Fuck- fuck- f-uh-fuck," You chanted, eyes closed and so close. She didn't panic, she just relaxed her throat and let you fuck her mouth. And realizing that made this even hotter for you. Finally with one last thrust, you spilled into the back of her throat, letting out a moan so loud it was almost a scream.

You dropped your arms, and ever muscle in our body relaxed... However, Viv/Syl decided that she wasn't through, and continued bobbing her mouth on your dick. You closed your eyes, enjoying the feeling as she got you hard again almost immediately. Feeling your strength come back, you sat up, placing a hand on her head again and pushed her down. You held her there for a few seconds before letting her pop off with a groan. You then placed your hands on her face and pulled her in for a kiss, letting the salty taste of your cum enter your mouth with her tongue. She broke the kiss to yank your pants completely off, as you slid her ripped leggings down her as well.

Now you're both completely naked, making out as she hooks a leg over your hips, pussy just out of reach. She grinds against you making you moan into her mouth. You feel yourself get harder as she does this, then her mouth moves to your neck. She grinds harder as she sinks her teeth in, every nerve you have is on fire. You can't take anymore, and lift her up enough to slide your now throbbing cock into her, bottoming out instantly.

"fuuuuuck!" She cries wantonly. You'd be smirking if you weren't so focused on bringing you both to bliss. As you rock your hips up against her, she chants a series of "oh fuck", "oh shit" and your name. And while having her like this is beautiful, and holding her trembling body feels like no other, you _need_ a different angle. Without leaving her, you push the both of you down, laying her on her back. Then flip her over, so her ass is in the air and her face is shoved into the pillows. Her moans now muffled, you grip her ass tightly, and shove yourself back inside. You let your head fall back in total bliss, pumping in and out of her carefully, but rough enough to get her to cry out with every thrust.  
You keep up this pace for a while, as the heat begins to pool again in your abdomen. You lean against her back, planting kisses across her shoulders and nipping at her skin. She continues to moan into the pillows, and you can tell she's begun to cums on your dick. You pump harder, bringing yourself to the bring, before pulling out, spurting across her back.

Completely spent, and tired, you roll over next to her, as she falls asleep. You were ready to pass out yourself, when your phone gets a text message.

**Notes for the Chapter:**

> I made an important edit to the meeting of your character and the brunette. 
> 
> Made the rest of the story easier for me to write


	4. Chapter 4

Dean sat with Sam at the bar. He watched you leave with some perky brunette, and sighed. He downed his drink and promptly ordered another.

"Dude, you okay?" Sam questioned.

"Fine." Dean snapped. Cass hadn't been answering his calls, texts, prayers, nothing. Completely MIA. Dean was worried and just watched his "potential gay thing" leave the bar with a hot girl. But he wasn't about to let that bother him. At least, not obviously. "So this place-" he paused to down his second drink. "-is what our vics have in common?" 

"Well, both wives knew their partners went here before the robbery, and both suspects were regulars here....so-"

"So? What are we gonna do, test everyone with silver just as a precaution?" Dean questioned.

"No." Sam responded. "I've got a better idea. When this place was closed, I set up spy cameras around. They all feed back to my computer. When we leave the building, we can see whether or not the shifter is in the building."

"Smart thinking, Sammy." Dean grabbed the glass the waitress placed on the table, saying with a smirk, "thanks sweetheart."

Tammy nodded and winked, running her hand up his arm, which sent a wave of desire over him. He gave her his predator gaze... Dean decided if he wasn't gonna explore his sexuality, he could at least have some fun where he's comfortable. But when he looked back at Sam, he knew he'd have to wait another night.

"Alright, alright, come on. Stop looking at me like that, let's go." Dean says, avoiding eye contact. Sam wants to press further, but decides a public scene probably isn't the best idea. He leaves a $20 on the table as the boys get up to leave the bar.

\----

It didn't take very long to set up the computer and software to see around the bar. Dean was silent the whole time, letting Sam ramble on about how this all worked; his mind stuck on you, the kiss, who you left with, Cass, what he would say... Each thought going a mile a minute, leaving him with more self deprecating thoughts.

"Hey, dude, " Sam snapped his fingers in Dean's face. "You okay?" He looked worried.

"Wha? Yeah, I'm fine." Dean says.

"No you're not." Sam pesters. "You just let me drone on and on about spy software without telling me to shut up. What's going on."

"Nothing." Dean dismisses his words, refusing to look at him. 'i just... I dunno, worried about Cass."

"Does it have anything to do with that kiss from that guy?" Dean's gaze snaps to Sam's immediately, cheeks going red impulsively. His eyes go wide for a second before returning to bitchface, then he stares at the steering wheel of the Impala.

"I dunno what you're talking about," he says. Sam gives him the trademark bitch face.

"Dean, come on. You really think I didn't see that? You know I don't care what you do or who you're into..." He tries. Dean turns his head more, attempting to hide his embarrassment.

"Anything on the shifter yet?" Sam sighs, wanting to push more, but not wanting to push Dean back in any closet hes attempting to crawl out of.

"No, nothing yet... Oh? Wait a minute..." Sam leans closer to his laptop, seeing a sliver of light. Sure enough, he sees shifters eyes coming from a familiar face. "Got it."

"Finally." Dean groans. "Something to kill. Who. What's the plan ?"

"Uhh..." Sam hesitates... "Dean? It's Tammy..." Dean thinks back to her lingering touch on his skin.

"FUCK." He says out loud. Dean groans loudly in frustration. He _hates_ shifters. Especially when they steal his face. "Now what?"

"Same plan as before... We actually have the upper hand... If her- _it's_ -next target is us, then we can use the element of surprise. She'll have to keep you busy, right? Out of the way?"

"I suppose...?" 

"Good. I've got an idea."


	5. Chapter 5

Dean's eyes went wide, face flushing. Dean didn't ever blush... Ever. But this?

"No." Dean said quickly.

"Wait, Dean- now hear me-"

" **NO.** Sammy, No." Dean looked away, unable to hide his embarrassment that Sam would even suggest such a thing. He was barely comfortable exploring. There's no way-

"It could be our only shot! You know him personally, an-"

"Sam! Can you just drop it already?!" Dean shouted, not daring looking at his younger brother. Sam could see his ears were red from behind, yet sighed. After a small silence, Sam spoke softly.

"It touched him too, you know." He purposely focused on the camera, keeping an eye out on the shifter. Dean was silent for a little while longer before he spoke too.

"What?"

"The shifter," Sam tried to choose his words carefully. This wasn't about manipulating Dean into doing anything at all with you; this was about catching the shifter. And you were the perfect bait. "It touched him too. It was all over everyone, it could hurt him too."

Dean stayed silent, but closed his eyes. Fuck. He lost this argument, and he knew it.

Because Sam was right. The shifter has your DNA, and can now use "you"- your skin; your voice - to do anything. Rob anyone. Sleep with anyone... Even if Dean barley knew you, you were his first official gay kiss. The man who opened the door. The man he wanted to know more about... He couldn't live with himself if he passed on Sam's plan and you got hurt somehow. He couldn't do that even if he didn't know you at all anyway. His deep sigh let Sam know that he had won.

"Alright! Al-" he sighs again, "Alright. Fine. Just... I... I dunno, what am I gonna say...?" Dean's embarrassment was given away by his rosy cheeks. Texting girls? No problem. He can be the smooth guy till the world ends.

But a guy was whole new territory. He didn't know how you'd react. If you were even still interested... Dean pulled put his phone and stared at your name... A dozen instances went through his head, all of them ending in "no." 

"Just... Say hi." Sam suggested. Dean rolled his eyes and took out his phone. Dean's face goes red as he starts to type.

D: _Hey, (Y/n), it's Dean... From the bar the other night?_

He got a response from you about 2 minutes later.

Y/n: _Oh hey! :) I honestly didn't think you were gonna text me_

D: _I'm full of surprises... Can we meet up somewhere?_

Y/n: _sure ;) where did you wanna meet?_

D: _how about the bar?_

Y/n: _now?_

D: _sure, sounds good_

Y/n: _cool. I'll see you in 20 ;) xo_

Dean hid his face from his brother at that. He was surprised at how well this was going in all honesty.

Dean pulled the car back out front, into a parking space, his heart beating a mile a minute. That adrenaline feeling sank in again... He wanted to back down, take off... Not do this. But, he needs to catch the shifter. Dean, closed his eyes and forced himself to take a deep breath. And he needs to know for sure, how he feels around guys.

You've come across as a decent person. Decent enough that you wouldn't have to force Dean to hurt you if you tried some sneaky shit. Sam ran the plan by Dean one more time, as he reached into the front compartment of the car. 

"What's that for?" Sam asked.

"Insurance." Dean said. He placed it in his pocket before getting out of the car, Sam following behind him


	6. Chapter 6

You spot Dean standing outside of the bar. He was looking down at his crossed legs, leaning against the wall.

"Hey, Dean!" You said, smiling. The other guy in plaid (though he's wearing a white shirt, dark pants and a tie now) was with him too, holding his closed laptop. You went to introduce yourself to him, but the taller gentleman beat you to it.

"I'm Sam, Dean's younger brother." He said, holding his hand out. He had the hugest smile on his face, and you could see Dean turn his head out of the corner of your eye. 

"(Y/N)," you said, grabbing Sam's hand and returning the smile. Things were a little awkward... You weren't really expecting company, but you went with it as long as Dean was comfortable.

"Listen, buddy," Dean spoke, hesitantly. You stayed silent, listening. "This is, uh, complicated to explain..." He opened his mouth to explain further, but when his luscious green eyes met yours, he froze.

"See, we're undercover-" Sam pulled out his FBI badge, initiating your surprise. You caught the attention of a cop??? Hot as fuck. You had to focus to keep your arousal down. "-In that bar there, is a home invader..."

"Holy shit." You said. Well, that helped.

"We need your help to catch i-...her. Things might get a little weird-" You cut Dean off, holding up your hand.

"What do you need me to do?" You said, cooperating as best as you can. You loved the idea of helping people and putting a criminal away. _And_ you get to work with the sexy green eyed agent?? Fuck yes. Besides, how weird could it get? Dean chuckled. Fuck, he was so cute...

"Basically... We need you to flirt with Dean, and talk like you're rich." Sam spoke. "If you're up for this. The, uh, suspect will attempt to follow you to your home... We'll be waiting to take her down." 

You thought for a moment. Thinking over everything you've got. Most of your money is in the bank, all the booze was cheap, all valuables locked away except for the silver in the drawer, and you weren't exactly married to that... There was your laptop and Xbox, but you doubted that was something they'd look for.

"I'll do it." Which surprised them both. "Who's going in first? Me or you?"

"Hang on, let us explain a bit more before we jump the gun here. This is dangerous." Dean says, stepping forward. You make eye contact, and while his face turns a light shade of pink, he doesn't break his stoic expression. Dean begins to explain the plan in detail to you answering any questions you had. You tried to be as thorough as possible.

When you feel confident enough, Dean hands you a wad of $20's, and sends you inside.

\----

Surprise, surprise, Tammy is working again tonight. Her face lights up as you make your way through the door.

"Hey, babes!" You exclaim, making her smile bigger. "Glass of champagne please!"

"Ooo celebratin' somethin'?' She giggles, popping the bottle open.

"Hell yes!" You boast, imagining that this is exactly what you would do if- "I just got a huge promotion a work! Corporate now, baby!" You chug the champagne, while people start clapping. You were putting on quite the show and were secretly please at how natural you were at this. "Drinks on me!" you pull out the money Dean gave you, waving it around as the bar burst into cheer. "Open up a tab, sweetheart." You say to Tammy. "$500." You decide to throw a few extra of your own cash to really sell it. Plus, you figured, the FBI literally just paid you to get yourself, and a bunch of strangers drunk. What's a few extra shots? Tammy's eyes went wide for a moment, then a wicked grin spread across her face.

"Of course deah," She smirked. "Anything fah you." Her voice got lower and she gave you intense sex eyes. You were almost half-tempted to take her to the bathroom and fuck her right there but you had a job to do. Dean and his case were priority number one. You left Tammy hanging with a wink and a smile, and knocked back some fancy pink shot that tasted like watermelon. You have no idea who ordered it, but drinks were going left and right and everybody was happy.

After 40 minutes, 2 shots, two rum and cokes, one whiskey on the rocks, and a Kinky vodka with some kind of sour chaser... you... were... _hammered_. You kept the plan in the back of your mind, but it was quickly getting hazy as you chatted up everyone around the bar, kissed some random girl, and set the stereo playing some drinking song by Godsmack.

Dean walked in, seeing everyone drunk, happy, and dancing and couldn't help but smile. You sure knew how to sell this whole thing, and he was grateful for it. Dean ordered his own glass of something strong and dark. Turned out to be brandy chased with some kind of soda. You waltzed up to him. "Hey stranger," you slurred, wrapping an arm around his shoulder. He smelled good, you noted. The way the light caught his eyes made him seem almost god-like.

"Hey, (y/n)," he chuckled, patting your hand.

By this point, you forgot about the plan, your drunk fuzzy brain just knew you wanted him. You wanted to show him what it was like to be with a good man. Wanted to make him smile, just like that but wider. You leaned in close to his ear.

"You're looking fine as hell in that suit, babe." You whisper. Dean shuddered with goosebumps. He'll never admit that turned him on ever so slightly; his prime instinct being to tell you to fuck off. Retaining his composure, he let you continue. You run a hand firmly down his shoulder onto his peck, drawing pink back to his cheeks. A glass shattered in the background, but you were far too drunk to care. You were too busy thinking of things to do to see him smile... When an idea hit.

"Hey," You said, looking at him. He looked back at you, breathing shallow, fighting every instinct to allow this to happen.

"What's up, (y/n)?" He questioned, quietly.

"We shoul'go som'where," You say. Dean chuckled, that beautiful smile lighting up his face again. Your heart fluttered. 

"Like where?" Dean was expecting you to say your home. He could see Tammy watching carefully, while making more drinks. Shifters had great hearing, so Dean had no doubt that it could hear everything they were saying. Dean knocked back a shot of Bacardi, feeling a little safer that Sam was waiting outside at the ready. 

But then, you said something that caught Dean off guard.

"The beach." You stated, flatly. 

"The b-... what?" Dean said, confused.

"Yeah!" You grabbed his hand, intertwining his fingers in yours and pulled slightly. "It's right outside, lets go!" Dean, startled and confused, reluctantly followed your pull outside. He didn't want to fight you on this, especially in front of the shifter, but this wasn't part of the plan... 

You smiled and giggled your way outside of the bar, eyeballing the coastline and dragging him with you. Once you were far enough away from the building, Dean spoke harshly but quietly.

"(Y/n) what are you doing? This isn't part of the pl-" Dean was cut off, by the sensation of your lips pressed against his. Now that you both were standing, no seats or tables or bars in the way, you pulled him in by his face, keeping your lips against his longer. Dean's muscles tensed as his face went red, but didn't allow himself to deny how good it felt. After a minute, he allowed himself to give in to the kiss, pressing his own against you a bit harder.

"Follow me," You said, as you broke the kiss, not pulling away too far. Your brain was a little less fuzzy now, but you felt so determined to show him this. Something you rarely got to share with anyone. Dean followed you down the shore, embarrassed, but curious at this sudden turn of events.

Neither of you realized, the shifter following you out of the bar.

**Notes for the Chapter:**

> Little bit of fluff, and a little bit of crazy.  
> Only going to get fluffier and smuttier!


	7. Chapter 7

**Notes for the Chapter:**

> teaser fluff lmfao I'm sorry

Dean could still taste the booze from your breath on his lips. He took a couple deep breaths to calm the panic building in him. He almost wished he had time to drink more, maybe this would be easier if he were as drunk as you were. You led him down a mountain of stones, behind some beached trees. But what you were leading him to amazed him.

Tide pools. Dozens of them scattered everywhere. Most of them holding starfish and other sea life, but some? Some of the bigger ones glowed, with little moving organisms. It was almost like magic. The air around here was calmer... The mountains and dead trees keeping this spot a secret. Dean watched you climb down to one of them, eyeballing a little fish swimming around some seaweed. He couldn't help but smile a bit, watching the child-like wonder cross your face as you watched the fish swim around. Dean swallowed, and slowly followed you down. He hesitated, but climbed down to your spot, eyes flitting between you and the fish you were looking at. You looked back at him, then straightened up a bit.

"My mom... she uh... she used to take me here when I was a kid." You said. "I had moved away for a long time... But when I heard she was sick, I came back. But this place... I haven't been here in years." You sighed, keeping an eye on the tide pool. You didn't know the fascination with this specific one... There were fish in most of them. You decided to name him Kalvin.

"I'm sorry... About your mom." Dean said softly. He couldn't tell if you were still hammered or not. Honestly, you couldn't either. You just knew in this moment, it was you, Dean, and a lot of emotions. "I know how that can go... I uh... lost my own mother." He hesitated to say those words out loud. He didn't want to say he also lost his best friend at the same time, because explaining how he came back would probably be too much of a story for... A whatever first this was. Besides, Cass took off, and wasn't answering his phone.

Again.

Dean sighed. You looked up to meet his gaze, jaw tightening, then looked away. This wasn't the point of coming here... Yes, you wanted to get to know him, but you wanted to make him _smile_ , not upset. You pointed to a smaller log off in the corner of the crevice.

"Let's go sit." You say. Dean nods and follows your lead. You sit on the bench, but Dean surprises you both by sitting right next to you. In the awkwardness, Deans tie starts to feel uncomfortable, restraining his ability to swallow and move his head comfortably. He loosens it, drawing your attention. You look at his features in the moonlight. The contrast of night-black shadows with the dull blue-grey of the moon's light made him almost look like heaven. Dean looked up at the moon, staring so intently at it, it was like he was having an internal conversation. Maybe he was praying? You didn't want to interrupt. Instead, you put your hand over his gently. Reminding him that you're here, on earth, and he was here with you. He looks at you gently, but when you follow his gaze, you realize he's looking at your lips. He bites his own, takes a deep breath then asks:

"Can... D-do you think..." He coughs, then looks down. Then takes a deep breath and looks at you again, gaining his 'fuck it' courage. "C-can I kiss you again?"

You didn't speak a word, instead, you laced a hand around the base of his neck, and pull him in. You felt his muscles tense again, then he forces himself to relax. You keep your lips against his, gentle, patient. You're not expecting anything more than curiosity from him about this, and you were okay with that. Which is why it surprised the fuck out of you when his tongue traced your lips. You gently opened your mouth, allowing him to make the first move. Dean moved closer to you, letting his tongue explore your mouth, meeting your own. You circle his with your own, not being able to help the soft and gentle moan that escaped your throat. Dean surprised you again by wrapping an arm around your neck, making your own grip tighter as you both deepened the kiss.

Though you tried, you could barley help the growing problem in your pants. Dean was a great kisser, and you were sure he knew it. You pushed against him, having your tongue explore his mouth this time, as hit grip moved down to your shoulders. Slowly you broke the kiss, keeping your eyes close, not moving too far from his face. Dean swallowed hard, allowing himself to process the fact that he just made out with a man in a romantic beach setting. His stomach dropped, and he realized... Maybe there were some butterflies after all. But he couldn't deny that he enjoyed that a lot. And you were right; Lips were lips. Honestly, you were probably a better kisser than half the girls he's hooked up with. You stood up suddenly, pulling your shirt over your head. Dean was about to protest, saying he wasn't quite ready for _that_ just yet, when you zigzagged across the mine field of tide-pools. You abandoned your shoes by the beach, and dove into the water, Dean watching as you go. He shrugged.

"Fuck it," He said, shrugging his own jacket off, and pulling off his tie. His heart was beating faster as he pulled the white shirt over his head. Dean's phone went off as he was pulling off his socks and shoes, but he ignored it. Sam could wait a little while. If you had done your part right (and you overachieved on that bit, Dean was sure), the shifter would be nowhere near anyone else right now.

He waded in the water, slowly making his way to where you were swimming and watching the moon. Dean followed your gaze on his way to you. "It's beautiful." You say. Dean just nodded. You slowly wade over to him, wrapping your arms around his waist. Dean doesn't hesitate this time, and kisses you again.

_I could get used to this,_ He thinks, and wraps his own arms around you, pulling you close. You dip your hands to the hem of his pants, pulling his hips closer by the belt loops, making Dean blush. But by now, Dean feels ready. He's accepted that he is, in fact, okay with kissing boys. Maybe he's ready to do more? Whether he is or not, he wants to find out while he's still got the nerve. He wants to find out with you. Deans own hands dip lower, touching the top of your ass over your pants, making _you_ blush this time. The water splashes against your chests as a small wave begins to form. You debate picking Dean up by the hips, like you did with whats-her-name the other night... But you also didn't want to make him feel inferior. Instead, you settle for grabbing his ass completely, enticing a moan from the hunter. Dean unintentionally grinds against you, and you felt his boner through both of your pants; benefits of making out like horny-teenagers in the water. You both allow the water to pull you towards the shore, Dean allowing you to take the reins and put your hands all over him.

"I... uh... I-I don't really know how this whole... Thing works.. heh," He chuckles nervously. He didn't want to come out and say to do what you will with him and show him how to be with a guy, but he did want to drop the hint. You kiss him again, taking this as a green light to do what you've been holding back on. You lift him up with ease (thanks to the water), and wrap his legs around your hips. Dean yelps, face obviously red under the moonlight. You kiss him again, pressing on his lower back, to push his hips against you. "Relax. I'll show you," You whisper this offer against his lips. You could feel his erection grow harder against you at your words, and you kiss him again, this time, letting your tongue back into his mouth. Dean moans against you, holding on to your shoulders as the waves push you both to onto shore.

**Notes for the Chapter:**

> I'm actually not sorry at all


	8. Chapter 8

**Notes for the Chapter:**

> Ladies, Gents, and N-Binary's. The moment you've all been waiting for;
> 
>  
> 
> **SMUT**

Dean let you lead him against the sand, facing up at you and the stars. You placed yourself over him, kissing along his jawline and his neck, enticing moans from him. The waves continue to crash up against your legs, as Dean crawls up the beach a bit by his elbows; you following his lead as to not break the kisses. You trail them down his neck, across his adams apple and across his collar bone, making him gasp. Dean wasn't used to this... receiving attention in such a way. But, you were a giver, full and true, and you were gonna prove that to Dean. You trailed your tongue back up along his neck, feeling the stubble scrape along your tongue. Dean swallow hard as your lips landed back on his. He pulled your hips down onto his by the hem of your pants, grinding up against you at the same time. You gasped lightly at the friction, as you pushed your tongue into his mouth again. You felt up his sides as you both made out, feeling how taught his skin is, over every bump and ridge of muscle and rib. You tug at the front of his slacks, undoing the buttons, as he moans against your mouth again. Skillfully, you tease him as you trace more kisses down his neck, over his tattoo, and pull him out of his soaked boxers as your trail your lips gently down his stomach.

"Is this okay?" You breathe, voice deep, dying to taste him. He nods, breathless. You plant one more kiss as close as you can without actually making contact with his dick, as he sighs in extacy. Dean sits on his arms, watching you, trying to process the sight of a man- with a bit of a beard at this point -kissing down his abdomen, about to suck him off. You give him a devious wink before placing the head of his cock on your lips. You take him in agonizingly slow, causing Dean to throw his head back and moan loudly. Continuing the pace, you saver every groan and loud noise Dean makes at the sensation you're causing. You're a bit faster on your way back up, letting your hand follow you. Once your lips are off of him, you continue to work him with your hand. Dean's started to rut against your touch, needing a faster pace. You trace your tongue along the side of him again, before taking him down to the base in one swift moment.

Dean's arms go weak, and his back slaps against the wet sand. You move between his legs, fist continuing to pump him just so, as you get comfortable. Once you're settled, you place your mouth against him again. You can tell he's enjoying it- not just by the sounds he's practically yelling, but by his hands which reached up to hold your head as you bob, getting progressively faster. You flatten your tongue along the underside, sticking it out a bit further to reach the edge of his balls. You're grateful that he's shaved... or waxed... You're not quite sure, but either way, it's made this process so much easier.

"Oh god!" He yells, as he inhales through his teeth at the sensation. You continue this process; Going to the base with your tongue tracing him, all the way up to the tip where you flick your tongue against the top, letting him know what you're most skilled at using.

During this whole event, Dean's realized that he's being louder than he ever has been with anyone... He's practically moaning like a slut. How come he's never found a girl who could do this? How has he been missing out on this his whole life? His thoughts are interrupted by a change your pace; The faster you go, the louder Dean gets. The waves crash against your legs as the tide slowly starts to pull in. You quicken the pace, feeling his hips rise off the ground as the heat pools in Deans stomach. You reach down to pump your own insanely hard cock, as you take him down to the base, staying there. Dean gasps again, groaning as his spills down your throat. That pushed you over the edge yourself, causing you to explode over the sand. You swallow all of his, not letting your mouth leave his cock until you can feel it start to soften. Dean is panting like he ran a marathon, and twitching slightly. You can tell that was a pretty strong orgasm. He's laughing like an idiot now, hands up to cover his eyes.

"Holy fuck, (Y/n)..." Was all he could manage to say, before you pulled yourself up over him, and kissed him again. Dean hooked his legs around your hips as he gave into your kiss, giddy and high from the strong orgasm he just had. Dean pulled you down to him, pressing your body as close to his as you could get as he invaded your mouth again, loving this newfound guilt-free freedom of being able to make-out so intimately with a guy. You guys kiss for what seems like hours as the tide comes in, a wave crashing against the shore.  
You both seemed to have misjudged how far from the tide you were originally, as the wave crash over the both of you, causing laughter from him.

You succeeded in your drunken mission from last night; The genuine smile that spread across his beautiful face brought butterflies to your stomach. You smile back down at him, and kiss him once more; no tongue, just a normal kiss, as another wave washes over you both and almost pulling dean up by his ass. He laughed as he lifted his legs to keep his balance under you and his head above the water.


	9. Chapter 9

**Notes for the Chapter:**

> Chapters 6-8 from Sam's pov!

Sam got back in the car shortly after talking to you, Dean following afterwards.

"So..." Sam said in that annoying little brother 'I want details' voice. "That was (Y/n)?" Sam smiles.

"Shut up, Sam." Dean rolled his eyes, not looking in Sam's direction.

"What? He's cute," Sam teased. "I'll bet-"

"I said shut it!" Dean growled, turning on the radio. Zeppelin filled the car as he parked it around the side, out of sight. Sam rolled his eyes.

"Dean, you know I've got your back... 'swing that way', or not." Sam said carefully. "You're my brother. I've got you no matter what."

"Sam? If you don't shit your trap about (y/n), I'm benching you. I'll leave you at the motel and handle the fuckin shifter on my own." Dean cut the engine and sat there, nothing but Zeppelin filed the silence.

_ramble on!_  
I know my time, my time is now!  
Sing my sooong!  
I gotta find the queen of all my dreams! 

While Dean zoned out, Sam attempted to text Cass again. 

_Hey Cass, idk where you went, but we're on a hunt up near the border of Cali and Washington. Dean's...umm... Well he misses you, a lot. We both miss you. We're on a case at Carrie's Cafe, if you wanna catch up?  
-Sam _

Text sent. 

Dean was too caught up in his music to notice.

\---  
After about 40 minutes, the boys could hear the noise from the bar.

"I think (y/n) might've done a bit too good of a job..." Sam noted. Some blue eyed brunette wandered up near the doorway, curls bouncing near her face, and her little tan dress seeming too out-of-place for a bar like this... Sam squinted his eyes, but Dean didn't notice.

Dean was too busy putting the finishing touches to his tie, looking like a real fed again, touching up his hair in the mirror. Sam raised his eyebrows and Dean turned to stare at him.

"What?"

"Wha-? No, nothing." Sam raised his hands and leans back. "Nothing at all." Dean rolls his eyes.

"Shut up. It's to look the part, okay? This is about the shifter. Nothing else." But Sam could see the light rose color peak through his freckles. He was nervous to be around you, Sam could tell.

As Dean got out of the car, Sam pulled out his laptop, looking at the security footage to keep an eye on you , Dean and the shifter. But he couldn't help notice the brunette who parked herself not too far from him. She looked so familiar, Sam knew he'd seen her before somewhere...

After a few minutes, He watched you lean your arm over Dean, and lean against his ear.

"Aww," Sam cooed out loud. He was alone, so he didn't care. He always suspected Dean had a thing for guys. He just always thought he was gonna end up with Cass. Either way, Sam felt proud of his older brother for exploring who he was. Getting over the homophobia John had embedded in their skulls as a kid. 

Shortly after he saw the brunette drop her drink, which shattered on the floor. One of the bartenders ran over with a broom and dustpan as the brunette left in a hurry. Sam left the car, for some reason, and saw her outside crying.

"Miss?" She looked up, then rolled her vibrant blue eyes, wiping a tear from her cheek.

"Shit," she said.

"Wait... Didn't I see you leave with (y/n) the other night?" Sam inquired. She huffed softly and looked down. She nodded reluctantly, unable to stop another tear from falling.

"I'm sorry you had to see him like that... Guys like that just-" she cut him off.

"Sam!" He looked at her eyes wide with confusion. "It's me." The brunette sighed before Sam could ask how she knew his name. She crossed her arms and held them close to her chest, refusing to make eye contact.

"Uh... Me who?" Sam cautioned.

"Castiel."


	10. Chapter 10

**Summary for the Chapter:**

> Just a quick note: while Castiel's new vessel is female, ultimately on the show he identifies as male. Which is why I'm continuing using male pronouns when talking about Cass. Just to clear up any confusion.

"Cass?!" Sam shouts, caught off guard. Sam was unable to help himself- he stared at the beautiful brunette his Angel best friend was possessing. "Wh-... What happened to your...er... Usual vessel??"

Cass sighed and sat down on the curb. "Dean... He was having problems seeing past the male vessel... And, while I preferred Jimmy's vessel, Hope's seemed to be more of his style... I just... I just thought-... I didn't expect-..." Flashes of you and Dean went through his mind. Cass began to tear up again. Sam joined his friend on the curb, putting an arm around his now much smaller frame for comfort. 

"Cass..." He began. How does he even begin to explain? "It's not really my place to tell you this, but it's so obvious on him... He's exploring himself for you."  
Cass refused to make contact with Sam, letting his curls fall over his face. Cass didn't know how to process this. "Wh-... What?" He lifted his new face up, soft doe eyes looking back at Sam. He thought it was cute that Cass managed to find, what is essentially, the female version of his old vessel.

"The only reason Dean even considered doing anything with (y/n), is to see what it's like being with another guy. So he wouldn't disappoint you." Cass teared up, listening to Sam. He didn't really want to put words into Dean's mouth, but given everything that had happened, and with Cass suddenly coming back then taking off... Sam knew it had something to do with Dean and his feelings for the angel. 

"You're serious?" He said.

"Of course I am." Sam smiled. "Right now, however, they're trying to catch the shifter." Sam grabbed Cass' delicate new arm, helping him up. "But right now we need to get back in the car. We could blow their cover." Cass followed Sam back in the car. Cass wasn't used to being so short. Jimmy's vessel was 6" tall... This one, Hope? Was a whole foot shorter. It was very disorienting. 

Sam and Cass watch you and Dean take off out of the bar, shifter keeping it's eyes on you both. They watched you and Dean take off to the beach, which made Sam confused.

"What the.... What are they doing? This isn't part of the plan?" Sam fumbled around trying to find his phone. 

"Uh, Sam?" Cass stated, tapping his arm. Sam looked up at Cass, not being used to the new face, but then followed his gaze out of the window. Tammy was shifting, pulling it's skin off, re-locating every bone, muscle and tissue. Cass scrunched up his pretty new face, disgusted at the sight. He's seen the mess shifters have left behind before, but he's never actually _seen_ one shift. "Ew."

"Cass... This isn't good..." Sam stated, reaching for the silver knife in the compartment. The shifter didn't turn into Dean like they were hoping.

It turned into you.


	11. Chapter 11

Sam and Cass watched the shifter-you get into your car. It must know how to hot wire, unless you gave it your keys... Either way, it took off. Sam cut the engine on, and followed not far behind.

"Cass, can you look for my phone? We gotta tell Dean." Cass nodded, his curls bouncing in his face, as he rooted around the seats and compartments. Finally he found it wedged between his seat and the floor.

"Got it!" His voice squeaked, handing it to Sam. Cass blushed, then sighed of frustration. "I never liked being in female vessels... It's so disorienting." He huffed. Sam couldn't help but chuckle as he turned on his phone.

"Shit!" Sam yanked the steering wheel sharply to the left, trying to keep up with it. Sam had no idea where it was going, but thought maybe he could take a guess. If it turned into you, it was probably headed back to your place. Confusion struck when He found himself following the silver car into a construction site. "What the..." Sam trailed off. Absentmindedly, Sam handed Cass his cell phone. He took the closest turn to hide the car. "Call Dean." Sam said, as he grabbed the silver knife off of the dash and left the car. 

Cass looked at Sam's phone for a minute, but before he could even turn it on, he heard Dean's voice in his head.

 _Hey Cass... I... I don't know where you are, but... I've been, um... I miss you-_  
Cass' eyes widen and his face flushes. Dean's never said that before... not _to_ him, anyway.  
_I hope you're being safe, and... There's something I really want to say when I see ya again... I um... (ah damn how do I say this)... I've been 'testing the waters' so to speak... So... when ya get the chance, if you can hear me... Call me, okay?_

Cass' face went red, and at some point covered his mouth. He felt himself tear up at Dean's words. There was something different about this prayer. Cass could always feel some kind of emotion when Dean prayed to him, but this time... This time it was stronger. Cass forced himself not to get his hopes up- While he trusted Dean with all his heart, Cass couldn't really think rationally in a female vessel. Stronger hormones, and this one specifically was prone to very strong emotions... What's the phrase? Empath, he thinks. Cass swallowed again, flattening the dress on his legs and looked at Sam's phone. He wanted to call him right now, but Sam was going after the shifter alone... He opted to stick the phone in his pocket instead, and got out of the impala. He grabbed the other silver knife, following the older Winchester.

Cass used his grace to scan the area for the two beings. He could feel the shifter attempting to break into the back of the building, and he could feel Sam sneaking along one of the Ally's between the two large buildings- not even close to the shifter's location. He sighed, his breath pushing one of his curls out of his delicate face. Luckily, when Jack brought him back, the nephilim managed to repair his wings too- allowing Cass to fly again. He flew to Sam, making him jump. 

"Cass! Damnit, I almost shot you. Be careful." He whispered harshly. 

"It's not back there," Cass shot back. "It's back the other way." Cass went to go pull the hunter in the other direction, when they heard loud gunfire. A large chunk of the wall next to them exploded, cutting Cass' pretty new face. Sam yanks him back behind the wall, yanking him in the other direction. 

"The fucking thing has a gun?!" Sam shouts to himself, pissed at himself for not thinking of this. Cass takes out Sam's phone and tries to call Dean. _This is Dean's other,_ other, _cell, so, you must know what to do._

"Goddamnit, Dean! Sam and I need your help. The shifter's at some construction sight down town. It's shooting at us. Answer your damn phone!" Cass slammed the end button as he hid the phone back in his dress pocket.


	12. Chapter 12

Sam and Cass run along the side of the building. Sam was able to see that the shifter's gun was a basic revolver, and only held 6 rounds. It shot once, so he assumes it's got about 5 left. Cass looked around the dark, able to see much better than Sam was at the moment. But after the heightened adrenaline, and several minutes of silence, Cass realized something. Even if Dean did get their message in time, there's nothing he could do. He was stuck back there with you, wherever you two were. Cass furrowed his brows.

"Sam," He whispered. 

"What?" He said, not looking back at him. Sam had his own gun at the ready. Luckily, he had remembered to pack silver bullets, though, two seemed to be missing. He figured even with the two gone, they should be more than enough for the shifter. 

"Go back and find Dean. He's stuck there without a car. I'll stay and hold off the shifter." Cass replies. Sam turns back and looks at him.

"Are you crazy?" 

"No, Sam. I'm an angel, remember?" He spoke, harshly. "More importantly-" Cass was cut off by the sound of a large splash of water.

"What the..." Sam cautiously moves to the sound of the water, Cass following his lead. "Oohh fuck..." Sam trails off. His stomach drops as he puts his gun down slowly. 

"Dean's gonna be so pissed..." Cass replies in a morbid tone, as the hunter and angel slowly watch the Impala sink into the body of water. 

Suddenly, they hear an engine roar to life. Sam and Cass turn around, surprised by the sudden noise, just in time to see your silver car tear out of the driveway and down the street.

"Fuck!" Sam shouts. Cass sighs, defeated. "Dean... Is going to kill me."

"I'll just bring you back, don't worry," Cass replies, seriously, not even doubting that his hunter would pull a gun or something at the news of his car.

"I don't even know what to do first... Try to take off after the shifter, or try to get the car out..." Sam couldn't help but think what a smart fucking move this was as an escape plan. But now trying to think of the next step was like deciding which hot rock to step on. "Can I see my phone? There's no way we're gonna find the damn thing now. I gotta call Dean..." Cass took Sam's phone back out of his pocket, and handed it to him. Sam opened the phone, and called Dean again.

 _This is Dean's other_ other _cell, so, you must know what to do_

"Dean, uh, t-this is Sam... Listen, man.... I don't know where you are... But you're not gonna like it. Meet me by the bar? It's urgent." Sam presses end and sighs heavily. "Why isn't he answering, Cass?" Cass just shakes his head, dark curls bouncing from the motion. He pushes them out of his face.

"I don't know Sam," Cass looks back at the lake. "I don't know."

"Can you take me back to the bar? I told him I'd meet him there."

"Of course. I'll come back here and... see if I can pull it back out." Cass replies. He attempts to touch Sam on the forehead, but accidentally touches his throat. His eyes widen and he blushes. "Sorry, I'm still not quite used to how much taller you are now in this vessel." Sam chuckles awkwardly and bends down a little bit. Cass touches his forehead this time, and suddenly they're both at the Cafe. "Sam?" Cass says softly. He turns around and looks him in the blue eyes.

"Yeah Cass?" Cass bites his plump new lips and looks down. 

"Tell Dean... Tell him I'm sorry. For taking off... For everything." Sam smiled softly at him.

"You can tell him yourself when you get back," He replies. Cass smiles softly back at him. And suddenly, he was gone, and Sam makes his way inside the Cafe to wait for Dean.

**Notes for the Chapter:**

> This fucking chapter was physically painful to write btw. In several ways.


	13. Chapter 13

**Notes for the Chapter:**

> **smutty smutty smut smut**

You and Dean crawled up the beach a little, figuring there was still some time before the tide reached you two. You laid back, using your hands as a pillow and looked up at the stars. Dean still felt this butterfly feeling in his stomach, but figured since tonight was full of shit he didn't normally ever do- ever... He'd try something. He zipped back up his soaked pants, and laid down against you, head laying on your arm. You smiled, and let your arm wrap around him instead, pulling him closer. Dean swallowed, but a hint of a smile flashed across his face. You didn't break your stare from the sky though.

"Aren't they beautiful?" You ask. 

"Yeah," Dean said, but he was looking at you. There was that feeling again... He'd get it every single time Cass was around. This feeling he'd been running from for years. Yet here it was, again, and with you. Dean hesitated, but wrapped his arm around your waist. He was so glad it was dark, because he felt his face physically heat up from the blood rushing to it. He didn't understand what it was about you... But he turned into this awkward and shy person instantly around you. Dean couldn't decide whether or not he liked it. You pulled your other hand out from your head and intertwined it with his. Damnit, he was sick of this. 

Dean was a killer. A tough guy. Rough around every edge. He's seen more shit than a war veteran has. He's shot the devil in the face. He's been a damn _demon_. Why would he ever feel anything close to shy or awkward? That wasn't him. Dean tensed his muscles, and huffed. You looked up at his face, seeing he was deep in thought.

"Dean? You okay?" You asked. Instead of answering, Dean untangled his hands from you. He got up, and climbed over you, pressing his lips hard against you. Taken by surprise, you kiss him back, your arms moving to hold him by his waist on their own. Dean kisses you harder, then pins your hands down above your head. You yelp against his lips, surprised (and insanely turned on) at this sudden dominance that's come over him. Dean grinds against your growing erection, getting him hard as well, as he shoves his tongue back in your mouth. You groan against him, kissing him back, rolling your tongue over his. He doesn't stay on your lips long, instead he starts to nip at your jawline down your neck, pausing to suck a huge dark spot right below your stubble. You moan loudly, that being one of your biggest turn-ons. He's got you pretty hard at this point, as your hips buck up into his. He folds your hands under her right, and uses his left to yank down your jeans.

"It's your turn," Is all he says, before he releases your wrists to move down. He places himself between your legs as he trails his lips down your body, nipping and sucking along the way. You're in total bliss; rarely do the men you sleep with feel the need to return the favor. Yet here was Dean, conquering his inner fears as he pulls you free of your underwear. You feel the blood rush to your face in anticipation.

Dean doesn't give himself time to hesitate. As soon as he pulls you free, his mouth is on you. You groan loud at the touch, your back arching off of the sand. Dean tries to do what he felt you doing, flattening his tongue against the base of your shaft, going all the way down to the base. Though, when he tried, he gagged and pulled off to cough.

"You alright?" You asked breathlessly, trying to lean up to look at him. Your breathing was heavy, and the cold breeze from the morning beach on your now wet cock has got you shivering ever so slightly.

"That uh... You made it look so easy," Dean chuckles slightly. He goes to try again, taking as much of you in as he can.

"R-relax your throat," You say, surprised you're even able to speak. Dean tries again, doing what you said. He was able to take you a bit farther, but still couldn't get down to the base. So, instead, he sucked on you harder on his way back up, enticing a loud moan from you. You place one of your hands on his head as Dean runs his tongue along the base all the way down to the bottom and using his free hand to start pumping your dick. You moan louder, grinding against his pace and pushing on his head just a little.

"Dean," You whisper.

"Yeah, sexy?" He growled, feeling a little more daring now.

"More- ooh- p-please." You beg, which surprised you. Begging isn't really your thing... But something about him taking control like this has brought out your deeply hidden sub. Dean smirks, pleased with himself, and lowers his mouth onto you again. He tries to do what he's seen in the porn video's hes watched; keeping a steady pace, hollowing out his cheeks every now and then as he bobs his head. You drop your hand to support yourself on the beach, letting your head roll back like his was. He's got you thrusting into his mouth now (his hips doing the same), chanting his name and a series of moans and whines. Dean pumps his hand along the parts of your cock that he can't reach, as your leg starts to shake. He knows what that means, and he goes a little faster to hurry you to completion. He reaches into his pants to stroke at his own dick, to help relieve some of the pressure that's built. He moans slightly as your dick starts to throb, keeping the quick pace he's built.

But he slows his pace slightly as he realizes: he doesn't know if he's exactly ready to taste another man's cum just yet... Does he try it? Does he pull off and jack you off until you come on something els-? Deans thoughts were cut off by you moaning his name loudly and the taste of something thick and salty slide over the back of his tongue. Dean's eyes went wide as he spits out your load on the sand, coughing. Your in total bliss as you focus on trying to keep your breathing under control. 

"S-sorry," You say between breaths. Dean chuckles, then moves up your torso to kiss your lips, pressing his bare chest against yours. You return the kiss with a smile, reaching up to touch his face. He plants his arms on either side of your head, propping him up above you. Dean pulls away, but stays close enough that your noses are still touching.

"S'good. How was that?" He asks you, a proud smile on his face as he looks into your eyes.

"That... was amazing," You breathe. "5 stars." Dean laughs, and you laugh with him. He puts his forehead on yours and goes to kiss you again, grinding his exposed and neglected erection pressing against you. However, the moment was interrupted.

"Oh Je- _Dude_!!"


	14. Chapter 14

"What the- Sam?!" Dean yelps, jumping off of you, leaving your half hard boner exposed, while frantically trying to cover his own. You cover yourself quickly, dusting the sand off your ass before pulling your jeans up. Dean tucks himself away, obviously both embarrassed and irritated with his younger brother. Yet, you can't help stare at him; The way the moonlight bounces off of his toned core and arms, the night sky making the shadows darker... Makes everything more defined. "The fuck are you doing here, Sammy?" Dean snaps, standing up.

"I was looking for you!" he says in a squeaky defensive voice, not even looking in the direction of the both of you. "I- d-uh, I heard yelling- Thought you were in trouble, but-" Sam cringed, He'd already caught his brother in the act years ago, he wasn't exactly thrilled to re-live that moment; especially with a guy. You stand up, keeping an eye on the tide. The waves will start to hit Dean's feet any minute, which means you two better go grab your stuff before you leave. You take off to do that, leaving Dean to talk to his brother. "Dean... We've got a problem" Sam says in a hushed tone.

"You're damn right we do!" Dean snaps. Just when he was about to work up the nerve to ask you back to his motel too... Dean was pissed.

"No, Dean, listen... Cass and I-"

"Cass?" Dean's attitude drops instantly. "You talked to Cass?" Dean felt a pinch in his chest.

"Listen! We trailed the shifter-" Fuck! Dean totally forgot... He was too caught up in the moment with you, he didn't even think..."-It took (Y/n)'s car to some construction site..." Dean gave a confused expression to Sam. You had walked up at this point, handing Dean his shirt and tie back. Dean shoved it back on as Sam continued to speak. "It shot at us." Dean's eyes went wide.

"It shot at you?? Did you get it back?? Did either of you get hurt?!" Dean's concerned tone made you wonder what you two were talking about. Oh fuck! The mission! Your face went red as you realized you totally pulled Dean away from work to suck his dick on the beach... _shit_!

"Cass' face got knicked. She's fine, but the shifter got away," Sam stated. Dean's face twisted.

"Wha- 'she'?" Dean asked confused. Sam's face made a look that can only be described as the 'shit, I can't believe I just said that' face.

"Oh, shit, I forgot you haven't seen'em... Cass- uh-... inhabited a new vessel." Dean took your hand absentmindedly, leading the three of you back up to the logs. The tide was starting to come in more now, and if they waited any longer, they'd all be soaked. You and Dean are trying to hide the shivers from the morning breeze, but at least the shirts were dry.

"A female one?" Dean raises his eyebrow, pausing just enough where you're now in the lead, taking his hand and leading the brothers over logs and across the beach.

"Yeah... But um... Dean... there's something important you need to know." Sam hesitates, he almost doesn't want to tell him because of the look on his face. Dean lets go of your hand once they're over the logs and back on solid ground. He stops, and Sam gulps, but reluctantly starts to speak. "Th-the car.."

"What about the car." Dean growls, his expression going dark. Sam hesitates again. "Sam, what happened." This was not a question. This was laced in threat. Sam swallowed hard.

"The shifter... I-... C-cass and I were trying to find it-.." Dean cuts him off.

"What. Happened. To my car." His voice deepened. You'd be turned on if it weren't for the violence threatening in his eyes.

"The shifter... d-drove it into the lake nearby..." Sam said slowly. Dean's eyes went wide and he froze. There was a lot he had to take in tonight, but this by far was the hardest to grasp. He felt this pit open up in his stomach. He went to go speak, but no words would come out. He reached against Sam feeling dizzy, then realized he was forgetting to breathe. "Dean! Dean! Relax! Cass is getting it out... It'll be fine." Sam swallowed, preventing his brother from falling over. Dean said nothing, but gave him the darkest stare. He could see red, how pissed he was. That fucking shifter was **dead.**

\----

Cass flew back to the site of the lake. The shifter didn't seem to drive the car too far into the water; The trunk wasn't touched at all, and half the back tires were still visible. But it was far enough in there, that lifting it out was gonna be a bit of a struggle. Cass sighed, feeling under the back of the car for a solid spot to grab. He pulled, managing to drag the car out just a bit. His curls blew into his face, and he blew on them to shoo it away.

"Fuck this," He said out loud, charging up his grace. Castiel's eyes shone a bright blue, the gold light from his halo leaking through his tiny vessel. He grabbed onto the back of the Impala, and yanked hard; the motion pulling the car from the water most of the way. One more tug, and Baby was back on dry land, safe and sound. At least Dean wouldn't have a _total_ brain aneurysm. His light faded, the shine from his eyes disappeared, and Cass dusted his hands off with a smug smirk.

Suddenly, all around him was hot fire. Cass looked around, shocked and caught off guard. "What the-" He spun, until he landed on Dean's face. Cass squinted, trying to get a better look. Sure didn't /feel/ like Dean's soul.. "Who are you?" He said.

"Name's Tammy." The shifter replied. "And You're Castiel, Angel of the Lord."

**Notes for the Chapter:**

> I dunno what my obsession is with ending chapters with names or nicknames, but it also makes such a perfect cliff-hanger for the next chapter, ya feel?


	15. Chapter 15

Dean didn't speak another word. You swallowed, awkward, and a mix between slightly scared and slightly turned on. He was hot when he was aggressive, you couldn't help it. But the pure rage radiating off of him also warned you not to try anything until he could solve whatever was wrong.

"Uh... Sam, right?" You said, arms crossed over your torso. Dean was currently hot-wiring a car someone had left behind; probably too drunk to drive home them self. 

"Yeah..." Sam replied, nervously watching his enraged brother. Within seconds the engine roared to life, and Dean slammed the hood down with prejudice, and threw the driver side door open. 

"I ain't waiting around for you; Get in the fucking car before I leave you here." Dean snapped, looking at you two in the side mirror. You didn't even hesitate, leaving Sam standing there in guilty silence. You hop in the passenger side, closing the door behind him. "Sam?" Dean calls again. Sam just shakes his head.

"I'll um... I'll wait here-" 

"Sam. Get in the fucking car before I throw you in." Dean snaps. Sam jumped at the tone- it was very similar to the tone he used a lot when cursed with the Mark... Sam half expected this, but he didn't think his brother would really go that deep... He swallowed getting in the back of the car. Dean barley waited for the door to close before ripping out of the driveway.

"Directions." Dean stated. Sam pointed Dean down the road she shifter dragged them in. You hesitated for a bit, but once Dean had turned down Main st, You were sure.

"Uh... Why are we heading to my job?" You look back at Sam. His eyes go wide as he puts the pieces together. Sam stutters trying to think of an excuse, but Dean's 'give-a-shit-level' is in the negatives, so he's as blunt with you as possible.

"Because a shifter stole your good looks and memories and used them against Sam here." You blushed at 'good looks', but you stare at him.... There's no way you heard him properly. "Shape Shifter," Dean states before you say anything. "Look, I hate to break it to you like this-"Dean steals a glance at you, his expression softer than it was since Sam talked to him. "-Especially after... well everything that happened tonight." He sighed, you could tell he didn't want to do this. And he didn't. Dean wanted to spare you from this life. He barley knew you, yes, but he couldn't deny that there was _something_ there... He just hoped his job... This life wouldn't get in the way. He should've known better. 

"Monsters are real." He states. You raise an eyebrow, but you don't laugh like he's expecting. Instead you stay silent, letting him continue. "Vampires, Shape-shifters, Werewolves, ghosts, all of it. They're all real." Sam points Dean down the familiar dirt road of your job. Dawn is starting to break now, and you realize how tired you are. 

"So... I take it you're not FBI then." You say slowly. What the hell, you've got an open mind, and truth be told... You've always kind of hoped there was a little more to life. But you weren't about to call somebody crazy under any circumstances. Besides, he seems pretty pissed about _something_.

"No." He replies, simply. He sighs, a bit confused by your blatant acceptance, but also relieved that he doesn't have to fight to prove his sanity for once. Dean sometimes felt that every time he had to make that argument, not only does he ruin their outlook on life or sense of saftey, but also he finds it gets harder and harder to feel sane. "We're hunters." At that word, something clicks in your brain.

"Like those books!!" You shout. You've read Supernatural before, A friend had gotten you the collection for your birthday, but you had to sell them in a tag sale. Dean and Sam groan simultaneously. "What?" Sam sighs.

"Those books were about us..." He says with a monotone. You think back and remember, the characers names were exactly the same... Holy shit, all the pieces were falling into place. Your eyes go wide as you stare at Dean, completely star struck.

"Holy shit..." You breathed, not taking your gaze off of him. Dean throws the car into park, then gives you a devilish smirk. "I sucked Dean Winchesters dick. Holy shit."

"Oh come _ON_!" Sam whines, throwing his hands up in defeat. "Dude!" That seems to at lease alleviate a good chunk of Dean's sour mood, as he throws his head back into laughter. You touch your own lips in complete awe. 

Dean's body suddenly freezes as he looks dead ahead from where he parked. In what seems like a blind panic, he throws the door open, running out in a hurry. Sam and you open your doors, watching Dean race over to the '67 Impala, practically hugging it. "Baby!" he shouts, unable to help himself. "God, I was so worried," He said, looking over every crevice. There was still water dripping off of the hood and along the sides, but it seemed to be completely out of the water. Dean's head started spinning from the level of relief he had going on, and decided he'll check the engine for any type of water damage later. then Dean realizes something.

"Cass?!" He calls, spinning around. looking around the area. The half completed building dyed pink in the rising sun. Dean's heart started racing when he realized his best friend was nowhere around. "Sam, where's Cass?" 

"I-I don't know... He said he was gonna pull the car from the lake then come back with us..." He looked around himself, nervous. 

"Maybe we missed him when we took off?" You offered, shivering more through your completely soaked pants. The air was getting colder and you could see condensation when people spoke. Dean shrugged off his jacked, draping it over you, and gave you a warm smile. It was slightly forced, you could tell- he was worried -but the fact that he thought of you enough to give you his jacket made _you_ blush. You thought back to the conversation in the car. Wow... _Dean fucking Winchester_... You'd always pictured him to look hot, but the book didn't do him justice. He was beautiful. You lick your lips, in a trance, thinking back to the beach. 

Dean lowers his head, closing his eyes. "Hey Cass, we're at the construction site but we don't see you anywhere... Thank you for rescuing my car, first of all... Can you meet us here?" He pauses for a second, before opening one olive green eye and looks around. You pass a confused look to Sam.

"I'll explain later," He promises. You're still confused, but decide to let the matter drop. Dean closes his eyes again, and tries again.

"Cass? Buddy, you there?" His tone concerned, but when he opens his eyes again looking around, he takes on this expression that he can't quite read. Apparently whatever he was hoping to happen, didn't. "Sam, where is he? He's not answering?"

"I don't know Dean..." Sam asked, concerned himself. You look around, unsure what you're looking for. You're admiring Dean's sweet car, when you notice something weird by the bumper. You squint your eyes, wrapping Dean's jacket around you tighter. You walk over to the back of the car, noticing the clean and sleek circle on the pavement. 

"Uh... Guys?" Dean turns to you first before Sam does, walking over to where you were standing. Dean's heart drops at the sight.

"No..." He breathes, adrenaline taking over, but being out of options on what to do. "No... No no no no no..." His hands fly up to his hair as he fights back the sting in his eyes. Sam swallows hard, and you? You're confused as to what's going on, but seeing Dean this scared, it can't be good.


	16. Chapter 16

Watching Dean start pacing absentmindedly, you think back to the books. It's been years since you read them, and you vaguely remember a character named Cass. Wasn't he an angel or something? You looked around and realized you had to work soon, but left all of your work clothes at home. You went to reach for your cell phone to explain this to your boss, but then realized that you didn't have your phone on you at all. In a panic, you search back in the car Dean stole, but freaked worse when you realized it wasn't there.

"What's wrong?" Sam asked. 

"I can't find my fucking phone!" You exclaim. "Can I borrow one of yours? Maybe I can call it?" Dean doesn't say a word, but unlocks his and hands it to you. You dial your number and hit 'call'. It rings for a while, but eventually goes to your voicemail. "Shit." You say. "I must've left it in my car." Dean's eyes go wide, and you can see a glimmer of hope. 

"Sammy, get your laptop." He says quickly, grabbing his phone back. "(Y/n), What's your phone carrier."

"Uh, verison, why?" Dean's looking intensely at his phone, tapping away at whatever he's doing. Sam comes back with his laptop, and sets it on the trunk of the stolen car. He pulls up the website for the phone company, and pulls up a part of the site you've never seen before. Dean looks at you intensely.

"Listen. I'm gonna put you on speaker. You're going to tell them that your 17 yr old took off with your phone to party with their friends, and you're concerned because they haven't come home yet. You're able to go get them, but you need the gps turned on. Got it?" You nod, repeating his directions over in your mind. Dean pressed the call button and speaker phone. He held it out so you could talk, and kept an eye on you and the phone, ready to coach you if you get stuck. The call went smoothly, you told the operator exactly what Dean told you to say. Sam gave you and Dean a thumbs up as a location popped up on the computer. As you gathered around the computer, however, your stomach dropped. Apparently it was in the parking lot of a towing company across town; which either means the shifter is holding Cass hostage in a tow company building, or it abandoned your car and let it get towed. 

"Alright," He said. "Let's go." Dean and Sam took off to the Impala, but you hesitated. 

"Wait," That stopped them as they turned around to look at you. "We're just gonna leave this guy's car here?" The brothers looked at each other. "I'll drive it back to the bar." Dean nodded.

"We'll follow, then we'll go get your car." He agreed. You hand Dean his jacket back, then he hot wires the car for you again. He follows his brother back to the Impala, both closing their doors at the same time. You chuckle to yourself. You drove the stolen car back to where you found it, and as promised, the brothers followed. The lot was still completely empty, so it's safe to say the owner hasn't been around looking for it. You exit the car, but instead of hoping into the back seat, you decide to check on Dean, to see if he's okay. That internal desire to take care of him and see him happy is bubbling to the surface again, so you walk up to his window. He rolls it down, and looks up at you.

"What's up, (Y/n)?" He says, softly. You bite your lip, but instead of speaking, you lean down to kiss him. Dean widens his eyes in surprise, but closes them and gives into the kiss. Sam smiles to himself in the passenger seat. It was so gratifying to finally see his brother open up to himself. He was proud of his brother. You lean your forehead against his for a minute, then ask:

"Are you okay?" Dean swallows, still struggling a bit with being able to do this; especially in front of his brother.

"I'm fine." He states. You don't believe him, but you don't say anything. Instead you wrap an arm around his neck, hugging his head to you briefly before getting in the back of the car. Dean pulls out of the driveway of the bar, turning the radio on as he pulls back onto the road. After a few minutes of classic rock, You ask Dean a question.

"This radio have an aux plug?"

"A what?" Dean responds, confused.

"An aux plug. You know, put a chord in the radio and attach the other end to your phone or something?" You spot it as Dean was thinking to himself. "Oh! Found it! Can I play a song?" Sam does a double take at your boldness. Rarely does Dean ever let anyone touch his radio. Even Sam rarely got to pick out music. But Dean shrugs. What's one song?

"One. Then we go back to Zepp." He says. You find the chord in the back of Dean's seat, plug your phone in and plug the other end into the radio. This band was one of your favorites, and this specific song was a nice intro to someone who'd never heard them before. You sing along gently, so they can hear the lyrics:

_I can see you running, running_  
Every night from the same darkness  
It's coming, coming  
But you are not alone  
If you just say the word  
I'll be there by your side  
You make me more  
You make me superhuman 

Dean reaches for the volume, cranking it much louder, but quiet enough that he can still hear you as you start to belt out the rest of the words.

_And if you need me to_  
I will save you  
Send out the signal and I'll fly low  
If it means the death of me, I won't let go  
And if I'm lost in the worlds shadows  
I'll use the light that comes to me  
From your halo 

You're lost in the music now, completely forgetting your surroundings. You can clearly picture the sky and the stars in your mind, like you're reading a story. You started using the chair as a make-shift drum as you tap along perfectly to the beat.

_When you're backed against the wall_  
I could be the one who's always there to break your fall  
You are not alone  
You're the sun, you're the day  
The light that guides me through  
Never run, run away  
I will save you 

You're singing as loud as the song is, but arguably more passionately. Dean steals glances at you through the mirror, smiling to himself. He'd never seen someone other than himself and his brother so passionate about a song before.

_Send out the signal and I'll fly low_  
If it means the death of me, I won't let go  
And if I'm lost in the worlds shadows  
I'll use the light that comes to me  
From your halo 

Dean starts to nod along, as Sam thinks about how nice this change of pace is. It's a little harder rock than he's used to, but he can admit a good song when he hears one. Dean smiles as you close your eyes, miming along to the solo, as if you're playing in the band yourself. 

_Send out the signal and I'll fly loooow_  
If it means the death of me, I won't let goooo  
And if I'm lost in the worlds shadooooows  
I'll use the light that comes to me from your haaaalo! 

Suddenly, your voice gets softer as you touch Dean's shoulder. You lock eyes with his in the mirror for a few seconds:

_And if I'm lost in the worlds shadows  
I'll use the light that comes to me... _

You break the gaze by drumming along with your fingers on the seat, as you lean back and close your eyes, singing as hard as you can.

 _From your haaaaaaaaaaaaaaa-looooooooooo_  
your haaaaaaaaaaaaaaa-looooooooooo  
From your haaaaaaaaaaaaaaa-looooooooooo  
\- I won't let go, I won't let go, **I won't let go!**

You gasp for air a bit, forgetting to breathe during that verse. Sam smiles wider at your obvious passion for this song, as Dean starts to chuckle, singing along quietly; He's picked up at least the chorus at this point, but keeps his voice quiet in case he gets the lyrics wrong.

_And if I'm lost in the worlds shadoooooows_  
I'll use the light that comes to me!  
From your halo!  
your haaaaaaaaaaaaaaa-looooooooooo  
your haaaaaaaaaaaaaaa-looooooooooo!!  


**Notes for the Chapter:**

> https://www.youtube.com/watch?v=01BsH0p_T8c  
> Starset - Halo
> 
> The song (Reader) played for Sam and Dean.


	17. Chapter 17

Sam applauded your performance, and you could hear Dean actually chuckling up in the front seat. Dean was actually debating on asking you to play another by them. He actually kind of enjoyed the sound not to mention the message. But as soon as Dean was about to speak, they were pulling into the parking lot of the Tow company. Sure enough, there was your car, right behind the locked fence. You don't wait for instruction, you get out of the car on your own and walk right up to the front door. Sam and Dean stay inside for the moment. They watch as you knock on the door and wait for someone to open up.

"(Y/n) Is actually pretty awesome," Sam notes. Dean just smirks and nods.

"Yeah, he ain't half bad," he replies, thinking of another thing you're pretty good at. As if he read Dean's mind, Sam starts moving his eyebrows up and down, and winks. Dean frowns and rolls his eyes. "Oh shut up." He says, enticing a laugh from Sam. Dean watches you carefully as the door opens and you step inside. At the beginning of the drive, you guys decided that you'd go in, and check the area, deciding on whether or not it looks sketchy. Given your overachievement the first time, he wasn't worried about you missing anything. He trusted you. 

"So.." Sam says cautiously. Dean doesn't break his gaze from the door, ready to bolt if he hears anything suspicious. 

"So what." Dean says flatly.

"So, are we keeping him?" Sam chuckles. Dean makes a face at Sam, then rolls his eyes and goes back to watching the door. "You know what I mean. We're not just gonna let (y/n) take off and never see him again, right?"

"Isn't that what we're known for?" Dean replies, focused. Sam adjusts in his seat, facing his brother. Dean sighs, knowing exactly where this is headed. Dean likes you a lot. He does. But he can also remember what happened every time he got attached to someone. Cassy, Anna, Lisa, Cass... While he enjoyed your company, and felt _that feeling_ around you... Dean wasn't ready to lose you. Which he knew is exactly what would happen if he dragged you into this life. It's bad enough he had to break you to the truth.

"Dean. I know it's only been a day, but..." Dean groans and faces his brother, taking his eyes off the door.

"But what, Sam? What do you want me to say? Yeah, great, I've 'opened up to myself more' or whatever, and yeah, okay, I like him. But Sam... We can't drag another person into the mess we call our lives. He's better off where he is." Sam frowns.

"No." Dean looks at him confused, yet unamused. 

"What do you mean, 'no'?" He replies.

"Look... Seeing you two around each other... He's good for you, Dean. I can't remember the last time I've seen you this happy. For this consistent amount of time. You can't even stay pissed around him, haven't you noticed?" Dean rolls his eyes. "What I saw on that beach... While it was incredibly disturbing, it was also sweet. You haven't looked at someone like that since Ca-"

"Drop it." Dean snaps. He managed to not panic totally hard about Cass' whereabouts until now. He tried to refocus on the door to take his mind off of it. _We'll find him_ , He assured himself. Though he was still pissed about Cass' new habit of taking off almost every time he comes back. It's like Dean never gets to see him anymore. 

"I think you and (Y/n) should go on a date." Sam says, matter-of-factly, ignoring his brothers warning. Dean shoots Sam a look, eyes widen.

" _Sam_." 

"You should. When we go back to the bunker, I'll look through the news and police reports for leads, you and (Y/n) go out. Have fun." Sam finishes the sentence with a smirk, and Dean groans. "I'm serious, Dean. Go be happy with someone for once. You deserve this." Dean swallows hard at those last words, but reluctantly sighs. 

It's not that he doesn't want to take you out. Dean's thought about date ideas for the two of you since your first kiss on the beach. Mini golfing, the movies, dinner... He didn't know, whatever two guys can do for a date. But that fear of getting you hurt or worse had already taken root in his mind, and his stomach dropped. Dean thought this all over for a little while. He answered Sam as he saw the front door open.

"Where would I even take him?" He says softly, watching you walk out of the front door. He watches your lips as they smile, unable to hear what you're saying to the owner. The owner pushes a button, opening the gates to the impound so you could get your car. Sam gets an idea, and pulls his phone out, tapping on the screen.

"How about this?" he shows the screen to his older brother. It's a listing for local bands playing around the area. Dean bites on his lip, in thought as he looks over the names and the dates of the shows. He decides as you look through your seats for your phone. He sees one for a set of 3 bands he'd never heard of, plus a classic rock cover band. The show date was set for 3 days from now.

"This one," Dean taps on the screen. There's no place to buy tickets, but it has an information panel, with the location, set times, costs, and rules for the venue. Dean takes his phone, screen shots the picture, then texts it to his own phone. He looks up as you come out of the passenger seat, waving your phone around. Dean couldn't help but chuckle at the face you made. You walked over to his window, as he handed the phone back to his brother. 

"Everything's clear in there," You reassure Dean. He nods in return.

"Thanks for checking." He says.

"Thank _you_ for tonight guys. It was fun," You smile. Dean feels those butterflies again, but panics because it sounds like you're about to leave.

"You wanna head back with us? Hang out for a little bit?" He offers. You smile. Fuck it, you're already playing hooky from work, may as well play hooky with a hot guy and his funny younger brother. 

"Fuck it," You say out loud. "I'll follow you then." You smile at him, and he returns the favor. You notice as he reaches his head up just a little, nervous to ask, but wanting to kiss you again. You catch on and plant your lips back on him.

"Aww," Sam coos again, smiling.


	18. Chapter 18

Your kiss with Dean is interrupted by a violent yawn. It's going on 24 hours that you've been awake now, and it's all starting to catch up with you. Dean looks at you then at Sam. Dean tossed the keys to Sam, and got out of the car. Sam caught them on reflex and looked at Dean confused. He'd just hours ago got his car submerged in water, but Dean's still trusting him to drive?

"Meet us at the motel. (Y/n)'s too tired to drive." He states, closing the door behind him. Sam scoots over to the drivers seat, putting the keys in the ignition. Dean wraps an arm around your torso carefully, seeing that you're starting to feel too tired to stand properly. Dean was used to going a day or two without sleep, so he felt more than comfortable getting you and your car back to someplace where you could rest easy. He walks you to the passenger side of your car, and makes sure you get in safely, then shuts the door. Sam pulls off in the Impala, as Dean walks around the other side and gets behind the wheel.

As soon as Dean gets in and starts the engine, you fall asleep, leaning against the window. Dean can't help but smile as this warm fuzzy feeling crawls through his body at the sight of you. He swallows, scared of what this means, but knowing he wants to protect you and keep you around from here on out. 

\---

When Dean pulls into the motel parking lot, he doesn't see his car anywhere. Dean looks around confused and suspicious because Sam left first. He leans against the car, taking out his cellphone. 

"Dean?" Sam answers.

"Hey, where are you? I thought you'd beat us here?" Dean checks on you, still passed out in the front seat. 

"I stopped to get some supplies, I'll be back shortly," Sam promised. 

"Alright, I'll see ya soon then," Dean hangs up then walks over to the passenger seat. He opens the door, hand out ready to catch you in case you fall over.

"(Y/n)?" He says softly, shaking your shoulder. You don't budge. He chuckles a little. "(Y/n), we're here, wake up." Nothing. Dean squints, taking your pulse just to be sure. Nope, you're good. Just that tired. "Okay," he mutters to himself. Dean opens the motel room door, propping it open with a chair, then goes back to you.  
He hooks his right arm under your knees, and slides his left across your back. You were a little heavy when not in water, but Dean still managed to lift you up and out of the seat. He carried you bridal-style over to the hotel room, placing you carefully on his bed, then goes back to close the door. Your pants are still damp and freezing, he notes. He hesitates, but thinks maybe you'd warm up faster if he helps you out of him.

"It's not sexual," he says to himself. "Just trying to warm him up." But he can't help the blush that comes over his face as he undoes the buttons keeping your jeans tied to your hips. He swallows as he yanks the cold and damp fabric off of your legs, exposing them. He briefly thought about doing the same with your underwear, but decided that was too far and covered you back up under the blankets. Dean shed his own damp slacks, balling the two up and putting them on a chair. Sam still wasn't back yet, though it'd only been a couple minutes. Dean's phone lit up, and he looked over to check.

Sam: _Decided to get pizza for later. You want your usual?_

He must be at a store, Dean thought, No pizza places were open this early. He responded "please", simply, before locking his phone back and putting it on the table. Dean yawned and stretched himself. Seeing you so dead to the world had him feeling pretty tired himself. He clenched his jaw, but decided to be bold and curl up next to you. You were probably as cold as he was anyway, the two of you could heat each other up. Dean lifted up the blankets, sliding into bed next to you, just as you turn over. You grumble something in your sleep, then draped an arm over Dean. He smiled, putting his hand over yours and rubbing his thumb over your knuckles lightly. Within minutes, he was asleep too.


	19. Chapter 19

**Notes for the Chapter:**

> *TW* PTSD, Alcoholism briefly

You briefly wake up sometime during the day. You have no idea what time it was, but you know your body is warm, curled up and being hugged by someone else. Dean groans softly next to your ear. You don't know what he's dreaming about, but you blush as he pulls you tighter to him. You hear some shuffling around, but don't want to risk moving and waking up Dean. You smile and sigh in content, slowly lulling yourself back to sleep. 

\----  
Dean groans awake, slowly. He inhales sharply before he opens his eyes, then yawns. Sitting up slowly, he sees you curled up next to him, and he feels his heart swell in his chest. Dean rubs his eyes, and looks around the room. The light is bright, So he assumes it's somewhere around noon, but it's quiet. The second bed is right next to this one, but Sammy snores lightly. It's quiet enough to know for a fact that Sammy isn't in here. Dean looks around confused, sitting up against the wall when he spots something on the table.

It's a little bag sitting on the table, with a little white note propped up against it. Dean squinted trying to see if he could read what it says from the bed, but no luck.

"Ugh, god, what did Sammy do this time?" Dean groans in his deep, sexy, morning voice. He almost didn't want to get out of bed, but the fact that he slept the day away, and woke up to a mysterious present from his own brother who he hasn't seen since 7am... He was too curious to stay put. Dean rubbed your arm lightly before attempting to get out of bed quietly. You moaned softly and hugged your pillow close to you as your head nuzzles it. "Aww," Dean chuckles. He smiles and the swelling in his heart gets a bit bigger. He stood there admiring you for a moment; your legs had wrapped the blanket between them, as you pulled your pillow down in front of you. It almost looked like you were hugging someone. Your shirt had gotten pulled up, so he could see every curve and dip of your stomach and sides. 

After a minute passed, Dean realized he was staring at you the way he always yelled at Cass for doing to him. But now he understood why, at least; Though he had a hard time imagining anybody admiring him the way he was admiring you. Flashes of memory started to come back in waves; The Mark, his time as a demon, the massacre of those bastards Claire found herself with, Lucifer possessing Sam, Lucifer possessing Cass- Bobby, Charlie, Kevin, His mother, his father-  
Dean coughed, attempting to shake the violent memories from his head. He frowned, walking over to the fridge. Sure enough, Sammy also made sure it was stocked full of Dean's favorite booze. He grabbed the whiskey and sipped it straight from the bottle, until he felt like he had better control over his own memories. He stood for a moment attempting to catch his breath, but put the bottle of whiskey down when he realized he was shaking. He sat down, waiting for the booze to kick in, and sighing slightly when he can feel the low low buzz in the back of his head. It took a lot for him to get drunk, but even feeling that basic fuzz made him feel better. You stirred again in your sleep, turning over and dragging the pillow with you.  
He then realized, he was sitting right in front of the little present Sam left behind. Dean grabbed the note, reading it carefully:

 _Dean & (Y/n),_  
_I got a different room down the lot to give you some time together to do what you will. Text me if you need me; Pizza and pie in the fridge_  
_x, Sam_  
Dean rolled his eyes, but looked in the bag anyway. His eyes widened as far as they could go as his face lit up deep red.

 _DAMMIT SAM,_ He screamed internally. Externally he was as quiet as possible as not to wake you up; Sam's "supplies" he was grabbing went as follows: Condoms, lube, _a fucking cock ring_.

Dean cringed hard away from the bag, and got off the seat so fast he knocked himself over. Dean yelped, surprised, awkward, and caught off guard. The sound of Dean yelping, then both him and the chair hitting the floor, scared you awake.

"What the-?" You breathed, wide awake and on edge. You look over the edge of the bed to find Dean faced down on the floor, defeated. "Dean?..." He doesn't say anything. "Dude, you okay?" Dean just shrugs, keeping his position. You can't help it; the act made you chuckle. You look up, and spot the bag on the table. "Ooh, gifts?" You go to get off the bed, and Dean bolts up, trying to keep the bag out of your line of sight, accidentally knocking it into the wall. The bag tips over, and out falls the condoms and lube. Your eyes widen as you start to laugh. "Oh my god. Dean, if you wanted to take it farther, you could've just asked." You chuckled. Deans face went red.

"I-... T-This wasn't.... Dammit Sammy!" Dean glared at the door, the only thing he could physically stare at since Sam wasn't physically in the room. Dean groan and pinched the bridge of his nose. "I'm sorry... My brother he... He's a bit _too much_ of a fan."

"Overly supportive brother?" You chuckle. Dean chuckles back, sitting up on the floor. He's got one leg propped up and he's leaning on it with the arm he's touching his face with. 

"Yeah, I suppose." He responds, looking at you.

"I get it. My sister was the same way when I came out," You say. You picture your sister. You and her look so much alike, only she was about 7 years younger than you. "She'd try to hook me up with every guy she met." You laugh at the memory.

"That's basically what Sammy's doing with us," He smiles. "I mean, I guess it's good to know he's got my back through this..." You sit up, interested in learning more about him.

"Why did it take you so long to come out? You're, what, 35?" You tilt your head, and Dean can't help but notice how you seemed to do it the exact same way Cass did when he was confused. 

"More like 38," He responds cautiously. You just nod.

"I'm 36," You say. He returns your nod. 

"But uh, well, my dad... He... Well, he had his views. And when he had his views-"

"It was his way or no way, right?" Dean just nods. He reaches for his whiskey again, taking a swig, and coughing at the burn. "I get it. That's how my dad was." You look away from him, picking at your nail as you offer some details about your childhood.

"My mom and dad split when I was a kid. I looked up to my dad, even though I barley saw him. He was always the 'cool parent'," You threw up air quotes around 'cool parent', and roll your eyes. "He's the one who taught me that music was everything. And I wanted to be just like him." You sigh. Dean sat in silence, then took another swig of whiskey. 

"I get it," He says. "Hunting... That was always my dad's obsession. Find the thing that killed my mom, take it out. Doesn't matter who gets hurt, as long as that gets done. But when we were kids? He was the coolest. Indestructible. He'd be gone for weeks, but he always came back." Dean's breath hitched in his voice. "But... I don't know, I think about the things he's said... The things he's done..." He shakes his head. "I don't know. I wish he took a different route." He sits silently for a minute. You sympathize, and join him on the floor in just your T-shirt and boxers. He's leaning against the mini fridge now, and you take a spot across from him by the bed.

"I get what you mean," You say. "I mean, my dad wasn't a hunter, but he wasn't a good person either. And it took me a long time to realize that." Dean looks at you, concerned when your voice broke. "I, uh..." You bite your lip and look down. "Without going into too much detail here, let's just say that my dad couldn't wait to get rid of me, so I left before things got worse." You swallow back the lump in your throat. Dean wasn't ready to hear your sob story. You inhale, as Dean makes the decision to sit next to you. He offers you the bottle of whiskey, in silence. You don't normally drink straight out of the bottle- you'd prefer it over ice to make it too cold to really feel the burn; makes it easier to drink. But right now, you don't care. You take a small swig, coughing at the burn once it's down. Dean rubs your back, then wraps an arm around your shoulder. You lean into his embrace, both of you looking at the floor.

"So, we've both got shitty fathers," You chuckle trying to lighten the mood.

"Tell me about your sister," Dean says, looking at you. You smile. Your sister was a card. She was a class A diva.

"She's always got a witty comment to make... Undoubtedly got that from me," You chuckle. "You'd look at her, decked out in pink, purple, sparkles, cats and emoji's... but then she'll say some shit that'll knock you off your heels." Dean chuckles too.

"Like what?"

"Well," You say. One story comes instantly to mind. "So, I got really into this show in my 20's, right? So I'm watching it downstairs by myself, and this guy who nobody likes pops onto the screen. I had heard the door open, so I paused it. So she comes downstairs-" You start laughing already at the memory, which makes Dean chuckle. "Sh-hah, she comes downstairs, takes one look at the screen, and goes 'oh look! It's the douche'!" You start laughing more and Dean cracks up right along with you. You both laugh, and you take another swig of Dean's whiskey. 

"I remember," Dean starts. "When Sammy and I were kids... He broke his arm trying to fly off the roof." He laughs. Your eyes go wide at this information, but you're already giggly.

"Why the fuck did he do that?" You giggle.

"We were dressed up as superheros... I was Superman, he was Batman. I jumped off the roof and landed in a dumpster, but he missed and fell on the pavement." He laughs more. "I had to drive him to the ER on the handlebars of my bike." You didn't realize, but you had somehow found yourself laying on his lap, looking up at his face. You admired his smile, even from this angle. 

"My sister did something like that," You laugh too. "She was chasing me around our room... She was just about 4 or 5 years old at the time- And she decided to try to jump on the top step... Well she slipped and fell all the way downstairs." Deans mouth dropped. 

"Was she okay?" He asked, shocked. 

"Oh yeah, my sister's a bad ass," You didn't even hesitate to reply. "She fell down those stairs, broke her arm, landed right-side up on her ass, and she _laughed_ " Dean raised his eyebrows in shock. 

"Damn, your sister IS a bad ass," He chuckles. "What's her name?"

"Josie," You respond. "I miss her." 

"Where is she now?" Dean's now stroking your hair, and looking down at you on his lap. You had taken his free hand, and were toying with his fingers and yours.

"She's with her dad and our brother. They're states away though, my siblings..." You try to ignore the pit in your stomach.  
_You guys were laughing 5 seconds ago, dammit, don't make this depressing again._ You yell at yourself.

" _Her_ dad?"

"Yeah, my parents got divorced when I was a baby. She remarried and had my siblings later. They're separated now though." You say, somberly.

"And your mom?"

"A few towns over."

"We can stop by sometime if you'd like... See your siblings..." He offers. "We drive all over the place all the time. A stop in your hometown wouldn't be too terrible if it's not completely out of the way..." He looks into your eyes, and your stomach drops. You remember reading about his road trip vaguely. You remember Dean being your favorite character in the book, but you never imagined you guys had so much in common.

You and Dean exchange stories for hours; You talk about your mothers, memories, interests and favorite days. You tell Dean about your love for music, proving to him how passionate you are about it. Dean talks about fixing up Baby for hours, explaining to you every detail about his car. You're impressed he's got ever detail memorized. After laughing and drinking for a few hours, you look up at him and tilt your head again.

"Why do you keep doing that?" He chuckles.

"Why me?" You ask quietly, ignoring his question.

"Why you what?" He strokes your hair.

"Why did you choose me to 'test the waters' with? What makes me so special?" You wonder. Dean takes a moment to think.

"Aside from your good looks, you were the first person to make a move. You were open with me from the start- I admired that. And when you kissed me... I just... It kicked down the door I've been...." He sighs. "I've been afraid to go down my whole life. I always thought that if that turned out to be true, my dad would leave and never come back. Or he'd call me a freak. Or worse." Dean doesn't break eye contact with you. "Plus, my needs weren't important. We didn't have room for what we liked... Dad always said The Life had no room for... dating. It was one or the other, but try to do both, and get the people you love killed." Dean's jaw tightened. You take his jaw, and pull him down to you, reaching up to meet him halfway. You kiss him deeply, and take your time. He wraps an arm under you so you're not straining to keep your torso up, as he kisses you back. Neither of you know who broke the kiss first, but once your lips were separated, he whispered to you.

"Thank you," He says.

"For what?"

"For setting me free. I haven't felt this open in... well, ever. It's nice." You reach up to kiss him again.

"You're welcome," You whisper against his lips, as he pulls you in for a deeper kiss.


	20. Chapter 20

**Notes for the Chapter:**

> *NSFW*

You feel a fire wash over you with this kiss. You break it just enough to adjust yourself; You stand up, then swing a leg over his, straddling his lap. You're on your knees, as you lean down to kiss him, hands gripping his face, pulling him into you. Dean grips your sides, sliding his hands under your shirt to feel your skin. You push yourself against his body, feeling yourself get hard, before you lower yourself. 

You move your lips to his throat, and kiss him tenderly at first. But once you can feel his growing erection against your own, you bite into his neck and grind against him. He grips you tighter, gasping against your neck. You nip and lick along his neck, throat, and collar bones, enticing light moans from him. Dean pulls your shirt off, so you're now only in your boxers. You press your lips against him again, shoving your tongue into his mouth, and grab his wrists. You guide his hands down to grip your ass, and he lets you; eager to let you show him how to please you. He grabs onto you roughly, and you moan against him, grinding against him again. Dean kneads your ass, slowly pulling down your boxers with every grab. You bite his lower lip, and he breaks into a smile.

"What?" You ask, breathless.

"You like to bite, don't you?" He growls, playfully.

"Do you want me to stop?"

"I never said that," As he takes this chance to pull you close by your ass, and sink his own teeth into your neck. You groan loud in surprise, letting him try these new things with you. Dean grips you completely, as he lays you on your back, crawling over you at the same time. You feel the blood rush to both your face, and your now painfully hard erection, as Dean trails kisses down your torso. He's not nervous this time; You can tell. Dean yanks your boxers, pulling you free. Your back arches the minute his hot breath was over your dick, and a deep groan escapes your throat as his mouth comes in contact. You're loving this dominant side of him, and you let him have his fun. 

Dean hits every spot near-perfectly. He still hasn't perfected taking you down to the base, but he clearly remembered what you liked from the beach, and used it against you. He held your hips down from bucking as he slowly dragged his tongue up your shaft, then across the tip. You can't help but shiver at this, then he takes you down again as far as he could manage. Finally, he decides to stop teasing, and bobs his head in the most _perfect_ rhythm. 

"Fuck, Dean," you sigh in pleasure, hands reaching to grab his hair. He keeps going until your moans get louder and louder. Once you start to feel the heat pool in your stomach, you lift him up to your lips. You don't want to come just yet. You want him to first, however way he wants. Dean shoves his tongue in your mouth, laying over you. He grinds against you, no longer afraid of feeling a hard cock against his own. You've opened yourself up to him and allowed him to do the same in a way nobody else could; Dean trusted you completely. You moan against his lips at the feeling of his hard dick against you, and all you want is him. But you don't want to just /ask/ him for sex... You don't know if he's ready, if he'd want to top or bottom, or just stick to hot spontaneous blowjobs. But before you even decide, he gets up off of you and heads over to the table, his dick tenting his underwear. Dean grabs the condoms off of the table, and looks at them.

"Are you sure?" You breathe. He nods and gives you a dirty smirk. 

"Yeah. I think I'm willing to give it a shot." He states.

"Grah- Grab the lube too," You say between breaths. "Shit's important." He nods and grabs the bottle off the table. He'll have to remember to thank Sammy later for the... present... later. "Which do you want?" You ask him. Dean looks at you confused.

"Wha-?"

"Top or bottom?" He looks around, unsure of what you mean.

"Do you want to _give_ , or _receive_ ," You wink at him. His eyes widen and his face goes a bit rosy. 

"Oh...uhh... I- I dunno... You pick." He says. You reach out for the condoms. You prefer to top anyway. Plus this way, he can pick up techniques on how to do things right instead of you having to coach him through it. Dean tosses them to you and reads the contents of the lube. You tear one open with your teeth, then slip it over your dick skillfully. Dean rejoins you on the floor, watching you put it on. He takes this opportunity to remove his underwear and begins to stroke his own dick. He breathes out lightly at his own touch, remembering the mind-blowing bj you gave to him on the beach. He closes his eyes, jaw slack with pleasure. You savor that moment, seeing the bliss painted across his face. You crawl up to him, sliding your hands from his sides to his pecs, pushing him over as you get near the top of his shoulders. Dean falls back, eyes watching you as he hits the floor. You remove his hand from his dick, and replace it with your own mouth, taking him all the way down. Dean cries out in bliss, as you hold it there. You can feel his cock throb in your throat as you slowly suck on him on your way back up. He's now breathing MUCH harder, and you slide up to his lips.

"Are you sure you're ready?" You ask him. He just nods, unable to speak words. "Baby, I'm gonna need a 'yes' or 'no'." Dean swallows.

"Y-yes," His voice cracks, as he tries to find it. You reach for the lube, popping it open and peeling the silver plastic off of the opening. "If at any point you need me to stop or you change your mind, just tell me." You assure him. He nods and pulls you in for another kiss. You drop the lube next to him so you could catch yourself on the floor. His legs are on either side of you, and you grind your painfully hard erection against his ass. Dean's breath hitches at the new sensation. You pause to see if he's okay with it, and are reassured when he wraps his legs around your hips. You force yourself out of his grip to sit up, grabbing the lube with you.

You pour a generous amount onto your fingers as you reach down between his cheeks. Once your wet fingers come into contact with his hole, he inhales sharply through his teeth.

"Is this okay?" Dean swallows, heart racing.

"Go," He says, impatient. That adrenaline feeling is kicking in again, and if they didn't start soon, Dean was afraid he'd chicken out. You slowly push a finger into him, hearing him whine lightly. You pay close attention to his reaction as you move your finger and out of him, spreading the lube as much as you can. God _damn_ he was tight. Though, what could you expect from a virgin? You apply more lube as you work your finger farther into him slowly, letting him get used to the sensation, and enjoying every whine and hiss he makes as you do.

Once your finger is fully inserted, you curve it up a little and you hear his breath hitch; Bingo. You flick that sweet spot a few times, watching his back arch and his moans get caught in his throat. You decide to take it up a notch by returning your mouth to his dick as you continue. Dean grips onto the floor, in both bliss and agony. He's never known pleasure like this before; This was a whole new level that he didn't know was possible. He can't focus on anything but the sensations you're causing him, as you flatten your tongue against his cock, while curving and straightening out your finger inside of him. You slowly pull your hand out, re-lubing, but this time slowly adding a second finger along with it. Dean's moans get more high-pitched, as his hips buck into your mouth. 

"Ahh-," He gasps once both fingers are fully inserted. You pull your mouth off of his cock to look at him.

"What I'm gonna do now is called 'scissoring'," You say. "It's gonna relax the muscles enough to make sure it doesn't hurt." Dean's barley paying attention, but he nods anyway. Dean licks his lips, then swallows hard- his throat feeling dry. You begin to move your fingers apart from each other, scissoring him until you feel his muscles begin to relax. Dean's gripping into the carpet, desperately, feeling like he'll float away on the pleasure. You apply more lube to his hole and your fingers, just as a precaution, but Dean doesn't mind. You withdraw your fingers, and decide to do something.

You trail your tongue from the tip of his dick, down the other side of his shaft, and slowly up his hips, abdomen, stomach, torso, pecs, and neck. Dean shivered your entire travel up, grabbing onto you. He's completely breathless and a wreck below you, and you can't help but feel a twinge of pride. 

"Are you ready?" You ask him. He nods, then remembers you prefer actual answers.

"Y-yeah," He pants. You align the head of your cock against the furled skin, applying just a hint of pressure so that he knows the exact spot it's in, but not enough to breach.

"Remember, If you need me to stop, just tell me." You don't wait for his answer, before you kiss him deeply. He moans against your lips as you push your hips in, slowly breaching his hole. Dean gasps, cheeks red, keeping his lips against yours; The way he's been moaning and panting was embarrassing, and he's trying NOT to sound like a girl the first time he gets fucked by a guy... But once your head pops all the way in, All of that thought goes out the window. Dean throws his head back, moaning wantonly, and you continue to push inside. You smirk at the sounds he makes.

Dean's lightly sweating, and panting roughly by the time you bottom out. You give him time to adjust to the full-ness, remembering how hard it was for you the first time. Dean lifts his head up again, needing to taste you somehow. You feed into his newfound addiction, supplying kisses against his lips, down his jaw, and biting his ear. Dean found that the most surprising- how good that felt.

"Do that again," he says softly. You oblige, biting and sucking on his earlobe, as he moans louder. Finally you begin to move your hips. You gasp at the friction finally helping ease the pressure, as you slowly work up a rhythm. 

The faster you go, the louder Deans moans get, and damn did you think his moans at the beach were loud. You covered is mouth with your hand, as you thrust into him harder, causing Dean's back to arch off of the ground. Dean's in complete and total bliss, barley aware of his surroundings. You and the sensations you're causing are all he can focus on. He can't seem to stop the wild noises that bubble from his throat as well as he thought he could. 

You're panting yourself at this point, never having had taken a guys virginity before. It usually either stopped at blowjobs or he was experienced. But this was a whole other level for you as well, and you were loving it. You replaced your hand over his mouth with your lips, thrusting faster and harder into him as you pressed your lips against his. Dean reached to hold the back of your neck, keeping you against him, as he reached down to grab your ass. The heat increased and you could feel it now.

"I'm close Dean... I'm close... So close," You pant against his lips. Hearing how lost you are in this trance has Dean close to the edge himself. You slam your hips against him a little harder, as he chants a series of your name. Finally, you go as deep into him as you can get, forgetting to cover his mouth. Dean's practically screaming as his cum spills over you and himself, and you spill inside the condom. 

As you start to go soft, you and Dean are huffing, out of breath. Your every muscle relaxes, and you rest your head against his chest, planting a kiss against him. Dean reaches up, to hold onto you in an embrace. You pull out, and lay on top of him, still breathing hard.

"How're you feeling? Was that okay?" You ask.

"It burns a little, I'm not gonna lie," He states. Fuck! Not enough lube... You'll keep that in mind for next time, assuming there might be. "But other than that? Wow... Never realized what I was missing...." He states in amazement. Dean yawns as the last of his muscle relaxes, and you and Dean soon fall asleep right there on the floor; tangled in each other's arms.


	21. Chapter 21

Sam took his time driving back to the hotel in the impala. Yeah, you were tired, but Sam knew Dean was a sucker for a cute sleeping person. It melted his heart, and he knew it. Suddenly, Sam had a devious idea: He chuckled darkly to himself, as he took out the gps on his phone. 

\----

Sam arrived at the store, making sure the car was locked before heading inside. 

"Can I help you today, sir?" A well-built gentleman with a tribal tattoo leaned against the glass counter. Below him were a collection of vibrant and multi-colored vibrators, some as small as a pill, others bigger than the average size. Sam noticed the rainbow pinned on the clerks right pec, before he noticed the major sex-eyes he was receiving.

"I'm not here for me," Sam replied. "Actually, if you can help me out? I'm looking for a few specifics."

"What do you need?" He leaned back against his chair behind the counter, crossing his arms, but keeping the smirk.

"Well, my brother is recently... kind of out," The clerk raised his dark eyebrow. "He's got a guy over our place right now, and I'm trying to.. basically."

"You wanna play the big brother prank and leave a surprise for him and his new boy-toy?" He chuckled.

"I'm not the big brother, but basically," Sam chuckled back. "Any suggestions?"

"Lube," Was the immediate thing out of his mouth. "And condoms. I'm guessing he's never done this before?" Sam shook his head, trying to think of the funny reaction Dean's bound to have to get over the weird fact that he's buying sex supplies in a porn store for his brother. "You're a thoughtful brother. So here's what I'm gonna do; Take the condoms for free. Safety is no joke, and no matter who you trust out there, it's better to be safe than sorry. Lube is over there, I suggest the oil-based ones. The astroglide is my favorite," He added. "Now, I don't know what type of lover your brother is, and I'm assuming you don't either... but if he's into the kinky stuff? Check those out." The clerk pointed to a small corner of the wall where there was just one sign: Cock rings. Sams face flushed. Suddenly he was having massive second-thoughts about this. "Or even if he's not, the look on his face would be priceless. Keep the receipt in case he doesn't want it." Those words made Sam feel a bit better, reminding him that this was more of a prank than a present. He grabbed one then placed it on the glass counter. The clerk put them in a nice little bag, and Sam paid for them. 

"Thanks for your help," He said, walking out the door. 

"Later sexy," He winked as the door closed, leaving Sam beat red and walking just a little faster. 

\------

Sam had stopped by the supermarket quickly to pick up the pizza he promised Dean, before heading back. He opened the door silently, hoping that you and Dean weren't... busy... So he could come in, but once the door was open and he only heard the light snoring of you and Dean, he stepped through completely. Sam put down the present carefully on the table, stashed bottles of Whiskey and beer into the mini fridge, leaving enough room for the pizza. Once he closed the door and finally looked up, that's when he saw you two- You were curled up, facing the wall in the fetal position, one arm under your pillow, the other holding the hand of his older brother. Dean had his arm wrapped around you completely, gripping your body close to his, the other arm squished up against the headboard, his face close enough to the back of your head, where all he'd need to do is purse his lips to kiss you. Sam smiled wide, his heart swelling in his chest. Not only did you both look peaceful, his brother looked _happy_. Sam rarely saw that, and couldn't help but stare for a moment at the sight. 

Sam went over to the desk, taking out a piece of paper. You stirred at the sound of the drawer, and Sam walked over to the table. After writing his note and leaving it against the bag, Sam left to go to the lobby, to grab his own room. 

\----

Sam got settled into his own space. The room was much smaller, and only had one bed, but it was sufficient. He sat at the table, pulling out his laptop to check the headlines. But, after hours and hours of looking, he was losing hope on finding a lead on Cass for the day. He did notice some demonic signs... some lightening storms outside of California, maybe that was worth checking out? Before Sam could click on the next image, however, he started to hear loud moaning. He tilted his head in confusion, being told the rooms surrounding his were empty... unless... Sams eyes went wide, but the _**hugest**_ grin struck his face.

"HE DID IT. OH MY GOD." Sam shouted to himself. He'd be so disturbed if he wasn't proud of his brother for stepping into this milestone. However, the pride short lived after hearing said moans get louder. He started laughing harder than he has in years, practically crying while going red in the face. He got back into his seat, plugging his headphones into his computer and cranking the music, still giggling for several minutes afterwards after the music successfully drowned out the moans and groans coming from his brothers room.

**Notes for the Chapter:**

> Sammy's such a proud little brother lmfao


	22. Chapter 22

**Notes for the Chapter:**

> I just found out how to insert photos here, so guess what's at the end of this chapter?! :D

You woke up to the sound of your phone buzzing. Your eyes were still closed, head against Dean's sleeping chest. He was so warm, you didn't want to get up. It wasn't until the buzzing turned to ringing that you panicked, and sat up. You raced over to your phone, hitting the "answer" button.

"(Y/n)?!" Your mom spoke. "(y/n) Where are you, your boss called? You didn't show up today?"

"Mom, mom, please relax," You sighed, voice straining. You got off the floor, and headed to the bathroom so you could talk without waking Dean. "Explain yourself, (Y/f/n), Where have you been?" You sighed. You didn't want to snap at her in her condition, but when she called you by your full name like a teenager, you couldn't help the irritation in the back of you skull.

"I was approached by a couple FBI agents," You heard her gasp, getting ready to cuss you out.

"MOM- mom, relax, they just wanted my help to catch a home invader. I'm not in trouble." She sighed heavy and audibly, stress vanishing from her voice. "It took a while, turned into an all-night thing. I meant to call my boss, but by the time I found my phone, it was dead." You hated lying to her. But you're pretty sure your mom didn't want to hear that monsters were real and you gave Dean-friggen-Winchester a blowjob on the beach, then went back to his motel room.

"Did you catch them?" Her voice was soft, worry still in her tone, but you couldn't say yes. Just in case something else happened.

"No, she got away, unfortunately. They're still looking. Listen, we're gonna be out of here in a few, I'll make a pit-stop at your house. Do you need anything?" You talked for several minutes, making a list of the groceries that your mother needed.

Dean had woken up, groaning on the floor and hearing your voice in the bathroom. He took this time to get his pants back on, looking at the spot on the floor where you two were only moments ago. He was still a little sore, but mostly in awe at the fact that he did it. He did it. He crossed that threshold he's been too scared to even go near his entire life. He felt a lot of things... happiness, joy, fear, anxiety, a bit of nausea... But most importantly, he wanted to tell Cass. His jaw clenched at the thought of his angel best friend. Dean hoped that maybe Sam was able to find at least something on the shifter or Cass. Maybe he'll go try to find the room Sammy's in...

You exit the bathroom, pressing "end" on your phone, and see Dean's feet just within eyesight. You trail your eyes slowly up his dark blue jeans, to his belt which sits just perfectly on his bare hips, the sight of his toned and bare torso making your breathing a little heavier, up to his tattoo placed perfectly between his neck and his collar bone, finally resting on his perfect face. His expression was confusing... so many emotions running across his olive green eyes. Your breath hitched at the sight of his quivering lip. It took all of two strides to be pressed against him, holding his lips to yours. Dean wrapped his arms around your lower waist, pressing hard against you. Dean squeezed his eyes shut tighter, savoring this moment, needing the solace you've been more than willing to provide for him since you've met. You can tell that he's upset, so you wrap your arms around his waist, letting him kiss you. You don't pull away, you don't move your lips, you just trace circles in the small of his back, letting him press his lips to yours. When he finally breaks from your lips, he places his head into the crook of your neck, not letting go of you. You lean your head against his bare and firm shoulder, now rubbing your hand along the side of his back in comfort. You didn't remember much from the stories, but you knew his affection... when he chose to give it, was not one to be taken lightly.

You didn't see this to be the type of behavior that he would portray. His arms tightened around you, but all of his other muscles relaxed completely. This made him a little heavier, but you were happy he felt so comfortable with you, and honestly? You've never felt more comfortable with anyone. The people you've dated or slept with... They were always usually so reserved. Never let you in fully. And affection? Forget it. Affection only came with sex; You learned that long ago, so you did your best to keep it that way. Though, truth be told, you loved affection and wished somebody would come along to give you stupid moments of affection... moments just like this.

So when there came a knock on the door, and Dean's muscles re-tensed, you felt this pain in your chest... You didn't want this moment, however short it was, to end. But, you swallowed and sucked it up, letting him go. You watched every muscle on Dean move as he walked over and unlocked the door.

"Oh, f- dude!" Sam recoiled, shielding his eyes and taking a step back. Dean rolled his.

"I've got pants on, relax," he snapped, walking back into the room to grab his shirt. Sam lowered his hand a bit to check hesitantly, then dropped it completely when he saw the coast was clear.

"So... I've been up all night looking for any signs of the shifter... So far nothing." Dean closed his eyes, defeated, and sighed. He shoved his shirt over his head. You sat on the other bed, pulling out your phone to text your boss, let him know you were sorry about today, and you'll call him later to explain. "But," Sam continued. "I did find a few different things. Some electrical storms, a few of the locals cattle turned up dead yesterday morning..."

"So, demon?" Your eyes shot up in confused terror. You looked at Dean first, then Sam, checking for a reaction.

"That's my guess. Just a few towns over, maybe we can kill it before it does anything." Dean grabs his gun off of the seat, stuffing it into the back of his pants. You can tell the gears were turning in his head.

"Alright. We'll go check it out after we bring (y/n) home." He spoke, flatly. His expression was stoic, and you could feel this stabbing sensation in your chest. Bring you home?

"I can go with..." You said softly. Your gaze never left Dean's face, so you could see when his head shot up. Dean looked at you in shock and horror.

"HELL no. We played a risk with you at the bar, You're not gonna get ganked by some black-eyed bitch because of me. You're going home." His back straightened, and you couldn't help but feel ever so slightly turned on by this dominance thing.

"While I appreciate the concern, Winchester," He recoiled slightly, eyes widening at your use of his last name. "I'm not a child. And I'm not some-" Dean cut you off.

"No, but you're inexperienced, and you've got an actual life. I heard you this morning, your mom needs you. Go back to her, get away from this life." Dean's jaw tightened and his eyes hardened. He doesn't want you to leave... not really, but there's no way he's gonna take you hunting. He's lost enough people that he cares for. You deserved better.

"Dropping supplies off to my mom? Takes 30 minutes, tops. She's got a nurse at home for the next few days while I was supposed to be out here for work." You counter, crossing your arms and flexing a little on purpose. He sees, and can't help but swallow.

"Do you even know how to shoot a gun?"

"Yes." Your answer catches him off guard. He stammers trying to find another argument, but you answer before him. You get off the bed, dramatically flexing to keep him distracted while you say, "I'm going. That's final."

You grab your stuff off the table and open the door. Sam stood their mouth hanging open with this huge grin across his face. You just left his older brother _speechless_ , and Sam's seen Dean give this speech to countless people over the years. Dean watched you go, feeling weighted to the floor. Sam just smirked and raised his eyebrows before following you outside.


	23. Chapter 23

Sam walked up to you, quickly. He couldn’t help the smile on his face, but tried to be as serious as he could.

“Demons are far more dangerous than a shifter…” He said.

“I’m far more dangerous than you give me credit for, Sam,” You counter. You grit your teeth as he memories come back, but you shove them away. Now’s not the time. “Do me a favor?” You speak before Sam could ask questions. 

“Uh, sure?”

“You drive. I’ve gotta get to the store and pick up stuff for my mom. I have the feeling Dean is gonna try to ditch me…” Sam looks down and smirks. That was exactly Dean’s plan. When he doesn’t want someone hunting, He’ll go out of his way to prevent it if he can. Sam hops into the drivers seat of the impala, shoving the keys into the ignition.

“I’ll do you one better,” Sam replies as he turns the key, The engine roars to life as Sam winks. He drives off just in time for Dean to run out of the hotel room, in a panic-stricken sprint.

“DAMNIT SAM!” Dean shouts, throwing hi arms up and groaning. You repress the chuckle in your chest.

“Looks like you’re stuck with me, there, handsome,” you wink and slide into the divers seat of your car. Dean huffs but throws his duffle full of his favorite guns and ammo into your back seat. Dean climbs into the passenger seat, pouting slightly. Sam’s been getting awfully comfy just taking off with Baby like that… He makes a mental note to set his little brother straight next time he sees him.

Dean was mostly silent on the drive to the store. You bet it was because he was bitching Sam out in his head over and over.

“You coming in?” You ask as you pull into the parking spot. Dean is silent for another minute before answering you.

“Yeah, fine,” he says and gets out of the car. You walk in with him, eyes searching for a cart. Once you find one, you head up and down every isle, seeing if there’s some other stuff you or your mom need. You spot this cute little stuffed moose, picking it up and eyeballing it. Dean starts chuckling and takes it from you. He goes to speak, but every time he starts to talk, he ends up laughing a bit harder. You can’t help but giggle at his smile.

“what’s so funny?” You say between giggles, looking at him confused.

“S-hah, Sammy what are you doing here?” He wheezes through the last word before cracking up completely. You laugh along with him; you don’t understand why it’s so funny, but seeing him smile and laugh like that brings warmness to your heart. You and Dean begin to wander around, making jokes out of the things you find. There’s a rack of footie pajamas in the men’s department; you tell him he’d look great as Ted, he tells you you’d make a bitchin Harley Quinn.

You take Dean by the wrist, dragging him to the music department, and scan the rows looking at all the albums you love, pointing them out to him. Dean watches you as you point out each one, listening as you tell him how old you were when you discovered it, what you were doing when that album was released, which songs you loved, which albums you loved the most.. And Dean couldn’t help but smile at the butterfly feeling in his gut, watching. He couldn’t place it exactly… Maybe it was how you remembered the details, maybe it was the way your eyes lit up at every CD cover… Or maybe it was something else. But Dean knew right then and there that you’d become one of the more important people in his life. And while this terrified him, it brought him comfort too.

Dean began pointing out the CD’s of his favorite bands. While he preferred cassette tapes, using the CD’s to talk about his music while they’re there was easier. He explained to you all of his favorites. Which ones his dad played the most in his car. But when he saw the Led Zeppelin album, he stopped speaking mid-sentence. He picked it up carefully, eyeballing it front to back.

“Dean?” You ask.

“This was one of my favorites… I had lost the tape a long time ago… Never seemed to be able to find a new one… Every store that carried it would sell out, and of course, we were never in the same place for long… I kinda gave up looking a long time ago…” His voice was awestruck as he eyeballed the cover. You took the CD from him and smiled.

“Let’s go,” you said gently, and took his hand. He smiled at you and gripped you back, following you to the registers. You places his CD on the belt first, followed by your mother’s requested items, then paid. But as you both go to leave, you hear a familiar voice that sends a chill down your spine.

“Hello, (y/n),” She states. Suddenly your feet feel cemented to the ground and a deep shiver of rage pulses through your bones. Dean takes another step before realizing you’re not next to him, and stops. “It’s been a long time.” You can practically hear the smirk in her voice as you grit your teeth.

“What the fuck do you want,” You snap, not looking at her. Dean looks at you, then at the girl… She tilts her head slightly, bone-straight hair flowing to one side as her crystallized hazel eyes stare at the back of your skull.

“Such hostility… You’re not still mad abo-”

“Don’t you fucking dare finish that sentence.” You spin around, enraged, pissed off, and shaking. Her face looks exactly the same as you left it; broken nose, shining hazel eyes, a taunting glimmer mocking you. A low smirk painted in deep red lipstick. She was just as beautiful and just as frightening. “You have no right.” 

Then the smell hit. Dean tensed his muscles, ready to pull the knife out if it comes to that. She smirked, and took a dramatic breath.

“Listen,” she said, sharply. “What happened to you wasn’t my fault.” She shrugged. It took all your will not to clock her right there. “As for your sister, well-”

“You finish that fucking sentence, I’ll go back to prison right here and now,” venom laced your voice. Dean recoiled slightly. He never would’ve guessed you had a side like this to you. Prison? You? He couldn’t see it. Dean stepped between you two, shoving you out the door.

“Come on, tough guy,” he says, grabbing your stuff with him. “Let’s go.” You were shaking, violently, teeth clenching to fight back tears. How dare she? How dare she even come near you. You got into the car without another word. “Maybe I should drive…?” Dean says slowly… You think in silence for a moment then nod. You get out and switch to the passenger seat, handing Dean the keys. You sit in silence, attempting to silence the rage within you. 

As Dean takes off, he thinks. That was obviously a demon, based on the smell and the way she was taunting you. He wanted nothing more than to kill the black-eyed bitch, but it was too public. Wouldn’t have ended well.

After a few moments of silence in the car, Dean turns the engine on, pulling out of the parking lot. Once a good distance away from the store, he turns to you, concerned.

"(Y/n), are you alright?" Worry fills his voice.

"No." You state simply. And you're not. You can't fight the memories and truth be told, all you want to do is get drunk and sleep. You want to call your sister, but there's no fucking way she'd talk to you. She hasn't in a few years now. You pull up the GPS directions on your phone to your mother's house so Dean can navigate without you having to speak too much. The energy had been drained from you completely once the anger subsided. You fell asleep moments later.


	24. Chapter 24

**Notes for the Chapter:**

> ***NSFW***

As soon as Dean was sure you were asleep, he pulls out his phone to call Sam.

"Dean?"

"Hey Sammy, so you said there was a demon in the area, right?"

"Uh, yeah, why?" Sam's concerned tone had Dean sighing.

"Because I think I found it." He states. "She and (Y/n) got into it at the store... I think there might be some history to them." He glances over at you again. You were stirring in your sleep, distressed and twitching. Dean placed the phone between his ear and his shoulder, then reached over to rub his thumb against the palm of your hand. You seemed to relax ever so slightly at his touch, so Dean left his hand there, propping his knee against the steering wheel for added assistance if need be. "She had mentioned something about his sister... and Sammy?" He paused for a minute. "(Y/n) has a record."

"As in...?"

"As in he's been to prison. Whatever this demon did to him and his family, he took the blame for it. And trust me, he's very obviously still pissed about all of it." He frowns, glancing at you again, then sighs. "I'm worried about him, Sammy... He worked himself up so much, he passed out."

"I don't know Dean... I'll meet you in town and see if I can dig up what happened online?"

"Sounds good... I'll meet you there." Dean hangs up, leaving his hand on you.

-

You and Dean are about 15 minutes out from the destination you had plugged into the gps. But, Dean had noticed that whatever you were dreaming about was getting violent. He pulled over on the side of the road, then un-did your seat belt. You were twitching hard, face scrunching up and groaning incoherently. Dean placed a hand on your thigh and shook lightly.

"(Y/n)?" He ask softly. That didn't seem to do anything. Dean bit his lip, taking hold of your arm, and tugging you over to him. Dean held you to his chest, pinning your arms by your side as you squirmed harder. "(Y/n)! Wake up, it's just a dream! Hey, shh, it's okay. Come back to me... please...." He coaxed you softly to consciousness, holding you tighter. You gasped loudly, desperate for air as you shot straight up from his grasp, panting and sweating. You looked around, scared before your gaze rested on Dean's worried olive eyes. Emotions hit you all at once... Sadness for what that bitch did to your family... Anger for what happened to your sister, humiliation for what you did and the trouble you got into because of it... You tried, but when that first tear snuck out of your eye, you broke. Dean pulled you closer to him, holding you close to his warm chest as you sobbed into his neck. You wrapped your arms around him, as he attempted to adjust, pulling you even closer. Dean's leg was now on the front seat as his back slid down further, and you pulled yourself up higher to lay in his arms. Dean said nothing, just let you cry into his chest and traced his fingers up and down your back soothingly. "It's okay, (y/n), I'm here," he whispered.

How could he even show you kindness? Part of you were sure he'd never talk to you again if he knew what you had done... Dean rested his chin on your head, holding you close, and rubbing circles on your back to comfort you. You had shown him patience with his coming out and getting comfortable... Had been nothing but understanding when he opened up. He'd do anything to make sure you knew that he'll protect you. Even from yourself.

"D-dean..."

"Shhhh," he squeezed you for half a second, silencing you. You just laid there in his arms for a good 20 minutes as the tears dried and the shaking slowly stopped. You looked up at his big ol' green eyes, and noticed a few things: 1, his stubble from the unshaven morning made him look twice as sexy, which you didn't think was possible until now. And 2) his pupils we're really dilated. If you didn't know any better....

Dean leaned down to kiss you just then. But this kiss was different than the previous ones you've shared. This wasn't experimental or lustful. This... This was comforting. Reassuring. He moved one of his hands up to the back of your neck, pulling you in closer to deepen the kiss. You moaned gently against his lips, grateful for the contact and comfort.

Something about the noise you made flipped a switch in Dean. He placed his hands on your waist, pulling you up against him, this time allowing you to deepen the kiss. You trace his lips with your tongue, pushing his shirt up slightly to feel his warm skin. Dean broke the kiss for a minute to pull your shirt over your head, toss it in the back seat, then returned his lips to yours, feeling your body with his rough hands. You moaned at his touch, mouth opening enough to give him access to slide his tongue in. You move your hips to align your growing boner against his, and he rutted his hips against you at the contact. Though, you slipped off the seat pretty quick, breaking the kiss with it. 

"Hang on," he pants, and reached down to lower the seat more. Dean pulls his shirt off, climbing in the back seat. He threw his duffle to the floor, and your shirt. After lowering the seat as much as he could, you climb in back with him, sliding your body against his and attaching your teeth to his neck. Dean gasped at the contact, wrapping one leg around your waist and stretched his neck out to give you a better angle. You bit down harder, sucking on the skin and leaving a mark. Dean groaned, gripping you tighter and boner growing harder. One your lips were off of his neck, you returned your lips to his. Dean tugged your jeans down, palming at your erection gently, enticing moans from you. You curve your hips, giving him better access to you. Dean ran his hands along your length for a few moments, before sitting up straighter. He laid you down against the seat, pulling your boxers down in the process. Your arms held onto the back of the seat for dear life as Dean lowered his head. His mouth was barely over you before your hips began bucking up.

Dean trailed kisses across your jaw, down your neck, and slowly in a straight line down your torso. Next thing you know, he's sinking his warm hot mouth over your erection, pacing himself as he takes you in. Your face goes red, as you close your eyes and moan. Dean's started to find a pattern that works best for you, so he practices; going slow on the way down, keeping his tongue flat against the bottom of your cock, then pulls up with his hand following and twisting at just the right angle. You gasp as Dean runs his tongue over your slit a few times before taking you back down again.

"Oh, Dean..." You moan, breathing heavy. "Dean, please." Dean comes back up slowly, hollowing his cheeks then pulling off with a 'pop'.

"What, baby?" He growls, lowly. That alpha tone lighting a dull fire in your stomach. 

"Faster. Please." You pant, putting your hand on the back of his head. So Dean does. He takes you exactly as he has been, but with every bob he goes a little faster. Now he's got you bucking up into his mouth, and he's attempting to relax his jaw and open up his throat for you, taking you in farther than he had been able to before. Dean gags a little, but remains calm as you bring yourself to release. You yelp slightly as you spill into his mouth, your arm muscles tensing, making you hold his head down enough for your come to shoot in the back of his throat. Dean gags again, but tries his best to swallow; most of it ends up dripping out of his mouth. Now slightly high, you open your eyes. The sight is beautiful... He's got your come smeared across his lips, dripping down his stubble-laced chin. He's breathing hard, lust in his eyes, and he's looking at you like he just asked you a question.

"(Y/n)?" He says again. You shake your head back to earth. You're still breathing hard, but you try harder to focus, relishing the buzz in the back of your head.

"Yeah?" Dean wipes his mouth.

"How was that?" You grip the hair in the back of his head, and guide him up to you. Once face to face, you kiss him hard, tongue invading his mouth as you reach down to palm his rock solid boner. 

"Better than I've had in years," You replied, breathless. You pull him closer, so now Dean is laying on top of you, as he reaches into his duffle. After some shuffling around, he pulls out the lube and condom's Sam had bought. "Are you sure?" You ask as you spot them.

"Can I try topping this time?" He asks, looking you in the eye. You're mesmerized by the lust-blown greens of his, making it difficult to speak. You nod simply instead. Dean kisses you again, as he uses the seat to open the cap to the lube. He sits up, squirting some on his fingers, then reaches down. Your breath hitches as his thick fingers make contact with your hole. It's been far too long since you've bottomed for anybody... You'd almost forgotten what it felt like. But when Dean managed to breach your hole with one lube coated fingers, you couldn't help but cry out in pleasure. Dean moved your leg so it was resting against his shoulder, and kicked the other off to the side. You did your best to relax, but it wasn't easy. You moaned the whole time Dean slid his finger into you, but once it brushed up against that sweet-spot, you couldn't help the impulsive violent jerk your body impulsively reacted to it. "Are you okay, (y/n)?" Dean asked.

"Don't stop. Please." Your voice cracked. Dean relished the moment; Your face as red as a tomato, spread out before him, one arm gripping the headrest tightly, and your back arching as you he shoved another lube-coated finger inside of you. You were breathing hard as he added more lube to his fingers and your hole, moving his fingers in and out of you. Dean kept going until he could feel your muscles tensing again, then slid them out of you. You whined as he took a moment to put a condom on.

"Give me a sec," He chuckles. Dean's face is pretty red himself, but he wanted this. He wanted you. Dean applied more lube to his aching cock and to your hole, before lining his head against you. Your breath hitched, and your arm reached out to grab his shoulder. When Dean started pushing, all self decency went out the window. You chanted his name with every aching second he was pushing into you. Even Dean couldn't help but groan in pleasure. He's had tight women before, but this was sooooo different. Better, even. Once he bottomed out, Dean was completely wrecked, as were you. He stayed there for a moment, letting you adjust and savoring the pressure around his throbbing cock. Dean's breathing grew heavy, and you pulled him down by his shoulders. If he wasn't gonna move, you decided, he needed to sate something else. You took his bottom lip between your teeth, applying light pressure as Dean groaned loudly. You pushed your hips up a bit, trying to coax him into moving, but he just moaned loudly at the sensation. Dean leaned down, taking your neck between his teeth and bit down as he started pumping his hips. The duel stimulation had your cock leaking with precum before long. You reached out to hold his arms, needing to feel as much of him as you can. Dean is in total extacy in this moment; the pressure around him, how hot and tight you feel, every moan and breath you take... It's unlike anything he's ever had. Dean picks up his pace, feeling the heat pool inside him, causing your moans to get louder. "Oh fuck, Oh Dean..." You're gasping. You start chanting his name in time with his thrusts, as he leans his forehead against yours. You muster up enough muscle control to reach up and kiss him again, holding the back of his head. Dean slows his pace just a bit, and within seconds he's spilling inside of you with a loud groan, you spill your load seconds later, panting and bucking your hips. Dean pulls out of you carefully, but continues to lay on you. He's out of breath, still feeling that buzz of pleasure in the back of his skull. He kisses you again, softly, and you kiss back. You're grateful for this moment, for him, all of it. You lay still, holding him in your arms, amazed he chose you. And Dean was no less than thrilled that you chose him back.


	25. Chapter 25

After having cleaned up (you had baby wipes in the back of your car), and tossed out the condom, You hugged Dean one more time before getting your clothes back on. Dean was silent the whole time, watching you. He loved what you did for him, and what you let him do with you, but you still had this…. sour demeanor. Dean could tell your mind was still stuck on that demon, so once you got your pants back on and buckled up, Dean took your arms and wrapped them around him. He held you close, pecking your lips before putting his forehead to you.

“I’m assuming you don’t want to talk about it… But if you ever want to, know I’m here, and I get it.” he spoke soft. His whisper kept his voice deep, and there was still a roughness from having exerted his voice. You nodded and held him tighter before letting go. Dean swallowed the lump in his throat, then climbed back into the front seat. You followed not long after.

—

Sam had sent Dean a text saying he was at a diner he had found in town and that he ordered a burger for Dean when you two get there. Dean just responded “ok” and opened the trunk to your car. The first person outside to greet you and Dean was Dianna, a toned Spanish woman, who was about the same height you were, maybe a few inches shorter. She had her dark hair pulled back in a loose ponytail, and was wearing slacks and a t-shirt. 

“(Y/n)!” She jogged to you, smiling. She pulled you in an embrace and gave you a kiss on the cheek. Dean slowed his actions to look busy, but wanting to watch this interaction. “Your mom and I were almost afraid you weren’t coming!” She chuckled. You faked a smile (quite well, Dean was impressed), and hugged her back.

“The store was crazy busy,” You lied. “I feel lucky we walked out of there with all of her stuff.” She smiled.

“You’re such a good kid,” She says. Then she notices Dean rooting around in your trunk. “And who’s this?” She winks at you and wiggles her eyebrow. You feel the blood rush to your cheeks a bit, and can’t help the bashful smile.

“That uh-… That’s Dean,” You hesitate to call him your boyfriend… You two met not even a week ago, but you both have shared so much and been so intimate… ‘Friends’ doesn’t seem to cover it, but 'best friends’ is too… It doesn’t do him justice. “I helped him out on a case… Was trying to find a home invader,” Dean listened carefully, ready to play along with any story you tell her. He double checked he had his badge in his pocket. “We didn’t catch her, but he stuck around and we got to talking… and….” You shrug and smile looking away from her. She made a noise that can only be described as a squeak, then hugged you again. She pulled away quickly, with her hand out in front of her- fingers crossed. “Fingers crossed this is actually a real something,” She says to you, her eyes shining with hope. She doesn’t give you time to respond before stepping beside Dean, taking a few of the bags, then practically prancing inside.

“What was that about?” Dean chuckles, grabbing the rest with one arm. 

“That was Dianna,” You sigh. “She’s a fan. She- uh- is obsessed with 'gay culture’, and forgets that I’ve dated women too…” Dean chuckles and you take some of the bags from him. “She’s a sweetheart though. She’s good to my mother.” You lead Dean up the deck, and inside the house, directing him to the kitchen. Dean puts the bags on the table, Dianna putting each bag away, one at a time.

“Mom?” You call. 

“I’m in here, (y/n),” She calls, followed by a cough. You swallow hard, and make your way to her room. She looks a little worse than last time; Her IV has a fresh bag, almost full, but she’s looking thinner. Her skin is paler, and she has more pillows stacked underneath her. You fight the sting in your eyes as you walk over to her. 

“Hey mom,” You whisper. You move to sit over by her side, as she opens her eyes again. She coughs, then reaches her arms out.

-  
Dean helps Dianna put cans and bags away into the cupboard. 

“So,” She starts, a smile plastered on her face. 

“So…?” Dean looks at her confused as he hands her a can of spinach. 

“You and (Y/n)?” she looks him in the eye, her head tilting with inquiry.

“Uh… I suppose? I-I mean…” Dean couldn’t help but feel flustered… He felt the adrenaline again, bubbling below the surface. He knew she was important, but he didn’t really have any answers for her… You and him weren’t a thing… You’d slept together a couple of times and had a mind-blowing experience on the beach. Hell, he was barley comfortable dragging you with him on this demon hunt, but you seemed to have much-needed intell. She took a step to him, and Dean couldn’t help but feel backed into a corner, making that adrenaline feeling worse.

“Listen,” she says quietly. “I know he’s got a few quirks… But he hasn’t glown like this in… years.” Deans eyebrows raised in confusion. This was glowing? You were miserable… faking. Even Dean knew that. He could only imagine how bad it got before he met you. “I don’t know who you are, but whatever you did, it’s working. He can’t afford to lose you.” The smile had completely faded from her face and worry struck. “I don’t know how long he’s known you… Maybe it’s not my place to ask, but he’s like a little brother to me. Elly is dying. Doctor said this morning she’s only got two months to live, tops…” Her voice trailed off. Dean took a breath and pushed her aside. She was right; It wasn’t her place to ask. but Dean cared, dammit, and just thinking about the amount of pain you’d be in made up his mind for him.

Dean found his way down the hall, until he could hear you talking. When Dean saw the room, he noticed you laying sideways against your mom, talking… Like a lost puppy and it’s human. He clenched his jaw, and stepped slowly. 

“Have you heard from her?” Elly asked, carefully. You sighed.

“No, mom. You know she won’t talk to me.” It was your mothers turn to sigh and she stroked your hand lightly. “I’d give anything… to have her forgive me. Anything. I miss her.” You say, voice breaking. Dean’s heart drops at this… You were clearly stronger than he gave you credit for… If this was your life before he met you, and you walked away with such confidence?

“Oh?” Dean looked up and saw Elly staring at him. “And who’s this?” You lifted your head, then sat up straighter when you noticed Dean standing there. You stammered, trying to think of something to say, when Dean spoke for you.

“I’m his boyfriend.” He said, a forced smile to hide the fact that his stomach was in knots. “I’m Dean, nice to meet you Mrs. (Y/l/n).” He walked over carefully to where you two were sitting. Your mouth was hanging open in shock, the butterflies in your insides going wild. Boyfriend?

“Oh! How lovely! It’s such a wonderful pleasure to meet you, Dean! Come in! Come in!” Her face lit up- well, as much as it could for someone who’s as sick as she is. You were still speechless, so Dean spoke for you.

“It’s nice to meet you too. (Y/n), here has told me so much about you,” He smiled. 

“Oh, dear, right behind you is a chair, go ahead and pull that up. Join us.” Dean did, and you couldn’t help but watch him. 

Boyfriend?

“So, Elly, I gotta ask. Is it true you used to ride motorcycles across the states?” Dean grinned, enticing her to reminisce. 

“Oh you bet your sweet ass I did!” Dean jumps at the word use, but couldn’t hold back the chuckle. “Let me tell you something, back then, motorcycles were built much different than they are today… We had to stop for gas so often, I could practically see my money flying by on the highway!” She chuckled, smiling at the memories. 

“Mom, what about the ducks?” You smile.

“Yes, yes the ducks! So Dean,” She faces him, her blue eyes meeting his olive greens. “There’s a pond in Michigan, a little remote space my group and I used to go to every summer… And one year we were lucky enough to catch the ducks. There were hundreds! One of them-” She paused to chuckle to herself. “One of them had shit all over my best friend, Mickey.” She burst into laughter, clapping her hands together. “Oh, Mickey was a dick, and so deserved it-”

“Mom!”

“What? You don’t remember him, He took off for Europe when you were 3!” She chuckled. Dean laughed too, reaching out to grab your hand. You blushed and met his touch, intertwining your fingers in his.

“Dean, dear, did (y/n) ever tell you the story about how his friends had dared him to go streaking down our neighborhoods street?” She chuckled. Dean’s eyes went wide and he looked at you, trying to picture it. He laughed and shook his head.

“No, I guess you’ll have to tell me.”

“It was the funnies phone call I’d ever received! His best friends mother had seen his penis flapping along in the breeze, while he took off down the road.” Your eyes went wide and face went red with embarrassment. “And this girl he had a crush on, what was her name again? Oh doesn’t matter, she had seen it and-”

“MOM.” You stood up, trying to block Dean’s view from her, but he got to enjoy your ass in his line of sight instead. “Alright, I think we’re good with story time.” You blushed hard. She chuckled.

“I’m your mother, I reserve the right to tell your boyfriend funny and embarrassing stories about you.” You roll your eyes and groan. “You love me.” She pouts and winks.

“Yeah, I do.” You mumble, “Pain in the ass.” You both laugh and you lean down to kiss her forehead. “I’ll be back to visit later in the week, okay? I can’t keep him from work long.” She gave you a somber smile, and held your hand. 

“I’ll see you then. Dean, It’s been so wonderful to meet you. Hopefully you’ll be back with (y/n)?” Dean nodded.

“Yes M'am, I will.” He holds your hand again. You turn to look at him, but as soon as your eyes meet his, he leans in to capture your lips. Dean still feels that adrenaline, but it’s making you smile more and it’s making your sick and dying mother smile like nobody’s business, so he can get over his own image for a few moments.

“Aww,” she coos. “You two are so cute. Alright, now scram. I need to get some beauty sleep.” You laugh, and lead Dean out of the room.

“Bye, mom. Love you.”

“Love you too, sweetie.”

You wave goodbye to Dianna, as you pull Dean outside by the hand, closing the door behind him.


	26. Chapter 26

As soon as you both are in the car, you turn to look at him, shock returning to your face.

“What?” He asks, genuinely.

“ _Boyfriend?!_ ” Dean looks down, blushing. He stammers, trying to think of something to say. 

“I..- Jus-… I don’t know…- It just… Felt right.” He says slowly, as he turns to look you in the eye with caution. He hoped he didn’t overstep his bounds with you in anyway.

“Listen, _Winchester_ ,” Dean felt a shiver of pleasure run down his spine at the way you breathed his name. “We haven’t even been on a real date yet… You want that title, hero or not, you’ve gotta earn it.” This boldness from you that came out of nowhere was quite the turn on. Though, Dean had some smart-ass comments to make of his own.

“Really? So then I guess the beach doesn’t count then?” He teased, chuckling.

“Nope! I was drunk, and sex was involved,” You challenged, crossing your arms. Dean furrowed his brows, and gave you a sassy smirk.  


“No it wasn’t, the closest I came to your ass was grabbing it,” He crossed his arms back, and you were unable to help yourself from staring at the smooth tone of his muscles.

“Dean, sweetheart, oral sex is still sex. It counts,” You laugh. Dean rolls his eyes.

“Fine. I’ve got a better idea anyway,” He smirks at you and winks his eyes. You tilt your head, confused. “Nope. Not telling. It’s a surprise until tomorrow, now.” Your eyes go wide.

“What’s a surprise?” You inquire, hoping maybe you’ll get some detail out of him to sate your curiosity. But he just reached down to turn the ignition on, and gave you a devious wink.

“Our second date,” He says simply.

–

The entire way to meet up with Sam, you pester him about what it could be. You’ve guessed everything you could think of, but he just won’t budge! Now you’ve started naming out intricate yet silly ideas by this point, which makes Dean laugh, but shake his head. Dean parks in front of the diner where Sam is, trying to hold in his laughter so he can stay in control of the wheel. Once he cuts the engine, you try again.

“Hmmm…. riding a hippo, in grass skirts, under the full pagan moon, while wearing coconut bras and playing banjos?” Dean bursts out laughing again, leaning his head against the steering wheel. You giggle harder and try again, “How ‘bout- How 'bout- Chasing midget sewer rats with tiny unicorn pens until they squeak rainbows out of their little rat nipples?” Dean’s now red in the face, and his stomach muscles are practically seizing. He can’t breath from laughing so hard, and you’re right there with him. After a few moments pass, you both feel like you’ve got your laughter under control… Then Dean hiccups, and you both lose your shit all over again. Dean holds up his hand after a few minutes, right as you’re about to speak again.

“Okay, okay, enough,” He laughs, then hiccups again. “'Come on, Sam’s inside.” You both open your doors, get out and shut them behind you. Dean meets up with you at the front of the car, taking his hand in yours. You grin up at him as you grip his hand back, walking through the front door.

Dean spots Sam right away, his burger by the front of the table, and the barbecue slammer on the inside of the same bench, waiting for you. You drop Dean’s hand and hurry over. You were starving, and couldn’t wait to eat. Dean’s grinning watching you, and following shortly behind.

“Hey, Sam! Thanks!” You say, sliding into the booth and wasting no time getting the sandwich between your teeth. Sam looks up, startled, then smiles.

“Hey, (Y/n),” Then looks up at Dean. “Where have you guys been? I’ve been waiting.”

“We had to stop at (Y/n)’s mom’s place. Drop off groceries. She’s a sweetheart, but her stories run long.” He chuckles, sliding into the booth next to you.

“They don’t run _that_ long,” You retort, mouth full of sandwich. Sam couldn’t help but notice the smile spread across his brother’s face. He couldn’t remember the last time Dean’s smiled like that, and smiled back at the sight of you two.  


Sam ran all the data he’s collected by Dean, while you plugged your headphones in. You wanted to listen to a specific song that entered your head as they talked- not realizing they were talking about Suzie. 

The thing you loved about your headphones, is that no matter the volume, it was noise cancelling. You can see the brothers’ lips moving, but you couldn’t hear a word they were saying.  


_What if I told you, life was built to break?  
What if I warned you, you can’t outrun your fate?_

You took another huge bite of your sandwich to calm the impulse to sing along. _  
_

_Would you believe with time comes grace?_  
In perfect light, in perfect place  
Every dream was mine to lose  
And that’s what it took to lead me to you  


Your eyes are closed by this point, and you’re chewing and nodding along. Dean glanced at you, then slowed his talking as he turned back to watch you. You were in this whole other world, and he couldn’t help but stare.

_So here’s to the heartache!_  
And here’s to the mistakes!  
We’ll drink to all the years, the tears that leeed to this place!  
So here’s to the heartache  


_What If I told you, That everything fades away?  
What if I hold you, but tell you there’s just no escape?_

You’re mouthing along to the words between bites now, and thinking about how the song kind of applies to you… Maybe that’s why it popped into your head?

_Would you believe with time comes grace?_  
In perfect light, in perfect place  
Every dream was mine to lose  
And thats what it took, to lead me to you…  


You steal a glance at Dean, he’s talking fast to Sam, his intense eyes catching the light just right, that the olive color looked far more emerald. You smiled ever so slightly.  
__

_So here’s to the heartache_  
And here’s to the mistakes  
We’ll drink to all the years, the tears  
That led to this place. 

Your leg is bouncing in time to the drumbeat and you open your eyes to glance around the diner briefly, closing them immediately afterwards.

_Here’s to the dark days!_  
It’s been a long wait  
We’ll drink to all the years the tears that lead to this place!  


_I suffer I bleed!_  
_Lose everything, I’ll get my wiiiiiiings_  
_I fall from belief, Fall to my knees and you will saaaaayyy  
_With time cooooooooomes graaaace__

____

-

The entire time you’ve zoned out, Sam and Dean have been talking. Dean tried to get your attention a few times, but you were so lost in your own world, you didn’t hear him.

“We ran into that demon at the supermarket,” Dean says quietly, just in case. “I don’t know what it did to his family… he won’t talk about it. But whatever it did, it messes him up just thinking about it.”

“I looked up his record online? It says he was arrested for drug possession and murder.” Deans jaw dropped as he looked back at you, mouthing along to whatever you were listening to. “Though, it looks like he was released when he was able to prove that he was defending his sister? I guess the judge took it easy on him.” Deans brows went up in surprise and sorrow. He could only imagine what that demon could’ve done…  


As he’s thinking this information over, Dean notices that one of the waiters has been looking at them for quite some time now. He reached back ready to pull his knife if he needed to, as he got up from the seat. The waiter smirked, flashing his black eyes at him, then vanished behind the emergency exit, and Dean’s movements got faster. You looked up from your food, confused, and pulled out one of your headphones.

“Dean?” He either didn’t hear you, or ignored you, either way, he sprinted outside. But once he got out there and looked around, he saw nothing.  


“Hey D-” was all the demon got out, before Dean had it pinned to the wall, demon blade against it’s throat.

“What do you want?” Dean snarled, as the back door opened again, you and Sam trailing out of it. Your eyes went wide, though Sam was calm. This was nothing new.  


“Just came to check out the new boy-toy of yours,” It smirked. “Looks good enough to eat.” It winked at you, and you recoiled. Dean pulled the blade away, ready to stab the demon in the chest, when it responded quickly- “Nuh uh uh. I wouldn’t do that if I were you.” Dean placed the blade point first against it’s chest, ready to push in. 

“And why is that?” Sam asked.

“Because,” It smirked, devilishly. “I’m the only one who knows where to find Suzie.” It’s eyes went black again, and your bones ran cold at the sound of her name.  


“Good. Well you can tell her where she is, and I’ll make your death quick and painless,” Dean retorted.

“You don’t want to know why she’s important?” It baited. Dean took it, figuring it’s a set up to a trap, but knowing killing two demons is better than ganking one and letting the one who fucked up your life roam free.

“No. Just want to know where she is.” The demon rolled it’s eyes.

“It’s with the shifter, Tammy,” Was all it said before it smoked out of the body it was inhabiting.  



	27. Chapter 27

You were in total shock... You could feel a sense of numbness taking over as you watch the black smoke rise and disappear into the daylight. You started to feel light headed and dizzy... Next thing you know, Dean's arms were around you, speaking to you in a panic.

"(Y/n)? (Y/n)!! Breathe... Hey, baby, breathe," He held you up as you finally remembered to breathe. You felt sick, like you were gonna throw up. You tried to speak, but you couldn't get any words out. Sam helped Dean place you carefully on the concrete to sit.

The rest of the moments went by in a blur: Sam went inside to pay, Dean refused to leave your side. Somehow you ended up in the back seat of the Impala, Sam keeping you company so Dean could drive. You fell asleep against Sam's shoulder, Dean looking back every now and then to check up on you. Sam had put your headphones in and was playing music off of your classical playlist on youtube to help you sleep calmly. 

"Thanks, Sam," Dean's voice cracked. His brows furrowed at the sight of you, and he clenched his jaw. Sam just nodded back, holding onto you for added support.

\---

When you opened your eyes again, Dean had you in his arms and was carrying you through a door. Your head was leaning against his chest, and he (once again) was carrying you bridal style. You didn't stir; You exhaled a bit harder, but nuzzled against his chest. Dean looked down at you for a moment, and creased his brow. He carried you down to a room in the middle of a hallway, having Sam open the door for him, then placed you on the bed inside. 

"Thanks, Sammy." He said, and he hugged his brother. 

"Anytime," Sam replied. "Is he gonna be okay?" 

"I don't know... I hope so..." Dean said, worried. "I'm gonna try and get some sleep... Keep an eye on him and all..." Sam nodded. 

"I'm gonna fix some dinner. Call me if you need anything." Dean nodded back and closed the door behind Sam. You had passed out again, turning on your side. Dean took his shirt off, and climbed into bed with you. He wrapped his arms around you and pulled you in close, pushing as much of himself against you as he could. He kissed the back of your neck gently before nodding off himself.


	28. Chapter 28

**Notes for the Chapter:**

> *NSFW*

_"And this next song goes out to our very own (Y/n)! Happy 32nd birthday, brother!" The DJ sang as the next song began. A dupstep remix of Zepplin's Black Dog bounced through the speakers, forcing your heart to match the beat of the bass. You were wasted, having the time of your life with your sister and friends. Josie had stuck a "birthday king" crown on you, and now everybody was buying you shots left and right._

_After an hour, You found Josie again, her hair was a mess and the ponytail was starting to come out from her whipping her head around so much._

_"Hey, (Y/n)!" Josie calls. She was drinking a lot herself, and stumbled her way over to you. "So.. I'm liiiike- way too drunk to drive home. I called Dad, he's'onna'm get us." You nodded, but as you swayed, you caught a glimpse past her._

_A woman was standing there, a type of clear drink in hand, and she was talking to the DJ. Her bone straight brown hair, fell perfectly around her shoulders, and she adjusted the strap on her bra poking out under her falling sleeves. You were mesmerized by her... Her jeans hugged her ass and legs perfectly, and her make-up made her look a type of scary-beautiful. But you were far too drunk to be intimidated. The worst she could say was no, right? You pushed past your sister, and made your way over to this mystery woman, licking your lips slightly._

_"S'cuse me, miss," You start. As she turns, her hazel eyes look up at you, luminescent in this dark environment. You were totally stricken, and the DJ started to play a new song. The lights began to flash to the beat of the intro, creating this strobe effect around the crowd. You lean in to talk by her ear so she could hear you. "Care to dance?" Mystery woman bit her plump, blood red lips and looked up at you. She grabbed your shirt collar and pulled you close to her, locking her lips against yours as the bass kicked in. Next thing you knew, she was dancing against you_

Something lately drives me crazy  
Has to do with how you make me  
Struggle to get your attention  
Calling you brings apprehension

Texts from you and sex from you are things that are not so uncommon  
Flirt with you you're all about it  
Tell me why I feel unwanted. _ _ _ _ _ _ _ _ _ _  
__________ Damn! _ _ _ _ _ _ _ _ _ _-_________ she presses herself up against you, hands clutching your chest, lips a hair away from your own, but in a second they're away again. _

If you didn't want me back  
Why'd you have to act like that  
It's confusing to the core

_She's dragging you to the back now, and you follow her in a daze. You don't even fight her as she pulls you into the woman's restroom, hands all over your chest, dipping under your shirt. Everything feels fuzzy, but there's something about this that felt just right. She pulls you into a stall, lips on your neck and biting hard as she undoes your pants. You were so turned on by this boldness; her desire and the fact that she knew exactly what she wanted. She drops your pants then drops to her knees before you could even speak a word. She moves with such precision. The only reaction you could think of at first is to grab the walls of the stall._

_As soon as you reach forward to grab her hair, she stands and turns around, grinding her clothed-ass against your now raging boner. You're moaning and running your hands against her smooth skin. In one swift motion, you had her pants and her thong down just enough to slide yourself in. She moans gently at the contact, rocking back against you. Shocked and in complete drunken bliss, you grab onto her hips and thrust into her. Her bone straight hair bouncing around her perfect face, as she looks back at you, moaning and groaning at every move you make. You feel your cock twitch inside of her, and she's now thrusting back onto you, picking up the pace you've set. Now you're slamming into her, practically backed against the stall wall, as she's moaning louder. She presses against you hard as you feel your release building up. Confused, you try to pull her away, but she stays put. Luckily, you were able to pull out in time to spurt down on the floor. You hear her sigh, but you were too drunk to really understand her intentions. You pull your pants up, as she pulls up hers, and fixes her hair. For the first time since you laid eyes on her, she spoke to you._

_"Name's Suzie," She states, simply, putting her hair into a pony tail and not looking at you._

_"Uh, (Y/n)," you state, memorized by her voice._

_"That wasn't too bad," Her gaze meets yours finally, and she gives you a devilish smile. "We should go out sometime." She says, lowly, running her fingers down your chest. You lean in to kiss her, she leans back, but places her finger against your lips. "Call me." She whispers against your ear, sliding a card into your back pocket. You just stare in awe as she winks at you, and leaves you behind in the stall, her ass swinging on the way out.  
_

_____________ _ _ _ _ _ _ _ _ _ _ _


End file.
